Transparent colourants and colourant compositions, and their use

ABSTRACT

The invention relates to a colourant composition comprising in a weight ratio of from 99:1 to 10:90, preferably a weight ratio of from 95:5 to 30:70, particularly preferred a weight ratio of from 95:5 to 50:50, a pigment of average particle size from 10 to 200 nm and a 1- or 2-phenylthio-substituted anthraquinones of greenish-yellow colour hue, lacking electron-rich N (III) , O (II)  and further S (II)  substituents on the anthraquinone ring. The compositions are particularly useful in patterned colour filters. Compounds wherein the 1- or 2-phenylthio group is substituted by SOR 10 , SO 2 R 10 , SO 3 R 10 , SO 2 NR 11 R 12 , CN, COR 10 , COOR 10  or CONR 11 R 12 , or the anthraquinone group is substituted by SO 2 NR 11 R 12  are also claimed, with a few exceptions. The invention also relates to a compound of Formula (III) or (IV), wherein at least one of R 1 , R 2  and R 3  is SOR 10 , SO 2 R 10 , SO 3 R 10 , SO 2 NR 11 R 12 , CN or COR 10 , or at least one of R 7 , R 8  and R 9  is SO 2 NR 11 R 12 , with the proviso that R 3  is not SO 2 NH 2 .

TRANSPARENT COLOURANTS AND COLOURANT COMPOSITIONS, AND THEIR USE

The invention relates to the field of pigmented colour filters.Normally, trichromatism is achieved by using one blue, one red and onegreen filter, or alternatively one yellow, one magenta and one cyanfilter. These filters must be highly transparent, homogeneous and ableto be prepared in a very uniform layer thickness with precise pattern.

The correct position and the absolute value of the transmission windoware very important parameters for colour filters. There is a desire forhigh transmission in the wavelength range surrounding the lightemission, coupled with as high as possible an absorption fordifferent-coloured light. In addition, there is a strongly increasingdemand for a higher display contrast (ratio of luminances in the ON/OFFstates).

EP-A-1 291 379 discloses optical films for plasma displays, comprisingviolet to blue anthraquinone type colourants and a near infraredabsorber. The purpose of using violet to blue colourants and infraredabsorbers in plasma displays is to correct the colour tone and avoidinterference with infrared remote controls by absorbing the undesirablelight emissions of the usual neon/xenon light sources at 590 nm (Ne) andat 850 nm and above (Xe). These optical films are homogeneouslycoloured.

WO-03/035770 discloses a process for making green pigment compositionsfor colour filters by kneading both components with salt in the presenceof a liquid.

JP-A-H05/331 378 discloses pigment compositions for colour filterscomprising yellow anthraquinone pigments of the formula

JP-A-2000/281 928 discloses pigment compositions for pseudo yellowcolour filters comprising anthraquinone pigments for example of theformula

C. I. Solvent Yellow 167 is a known solvent dye of the formula

Substituted derivatives thereof have been used for example asintermediates (US-A-2004/0232382), as pleochroic colourants for liquidcrystals (JP-A-2003/238963, DE-A-33 14 467 or GB-A-2082196) or asdisperse dyes for textile materials (WO-2005/024123), optionally usinginkjet printing (WO-2005/040492).

CAS Registry [73507-58-1] is a compound about which nothing else but theformula is known:

Further known compounds are disclosed in U.S. Pat. No. 4,359,570, U.S.Pat. No. 4,420,581, EP-A-0040 139, JP-A-S62/064865 and DE-OS-2200 115.

It has now surprisingly been found that the transmission of pigmentedcolour filters is improved by adding certain 1- or2-phenylthio-substituted anthraquinones of greenish-yellow colour hue,lacking electron-rich N^((III)), O^((II)) and further S^((II))substituents on the anthraquinone ring.

Thus, the invention relates to a colourant composition comprising in aweight ratio of from 99:1 to 10:90, preferably a weight ratio of from95:5 to 30:70, particularly preferred a weight ratio of from 95:5 to50:50, a pigment of average particle size from 10 to 200 nm and acompound of the formula

whereinR₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈ and R₉ are, each independently of allothers, H, Br, Cl, F, SOR₁₀, SO₂R₁₀, SO₃R₁₀, SO₂NR₁₁R₁₂, NO₂, CN, COR₁₀,COOR₁₀ or CONR₁₁R₁₂; C₁-C₁₂alkyl, C₃-C₁₂cycloalkyl, C₂-C₁₂alkenyl,C₃-C₁₂cycloalkenyl or C₂-C₁₂alkynyl, each of which is unsubstituted orsubstituted one or several times by Cl, F, OH, OR₁₀, SR₁₀, SOR₁₀,SO₂R₁₀, NR₁₁R₁₂, CN, COR₁₀, COOR₁₀ or CONR₁₁R₁₂; C₇-C₁₂aralkyl orC₆-C₁₂aryl, each of which is unsubstituted or substituted one or severaltimes by SO₃R₁₀, SO₂NR₁₁R₁₂, NO₂, Br, Cl, F, OH, OR₁₀, SR₁₀, SOR₁₀,SO₂R₁₀, NR₁₁R₁₂, CN, COR₁₀, COOR₁₀ or CONR₁₁R₁₂;or any of R₁, R₂, R₃, R₄ and R₅ is, each independently of all others,OH, OR₁₀, SR₁₀, SOR₁₀, SO₂R₁₀, or NR₁₁R₁₂;or R₄ is together with R₃ or with R₅ 1,3-propylen, 1,3-propenylen,1,4-butylen, 1,4-buten(1)ylen or 1,4-buten(2)ylen, each of which isunsubstituted or substituted one or several times by Cl, F, OH, OR₁₀,SR₁₀, SOR₁₀, SO₂R₁₀, NR₁₁R₁₂, CN, COR₁₀, COOR₁₀ or CONR₁₁R₁₂, or1,4-butadienylen which is unsubstituted or substituted one or severaltimes by SO₃R₁₀, SO₂NR₁₁R₁₂, NO₂, Br, Cl, F, OH, OR₁₀, SR₁₀, SOR₁₀,SO₂R₁₀, NR₁₁R₁₂, CN, COR₁₀, COOR₁₀ or CONR₁₁R₁₂;or R₆ is a radical of formula

or R₇ is a direct bond from C in position 1 or 2 of the anthraquinonesubstructure to R₁;R₁₀ is [C₂-C₆alkylene-O]_(n)C₁-C₁₂alkyl,[C₂-C₆alkylene-NH]_(n)C₁-C₁₂alkyl, C₁-C₁₂alkyl, C₃-C₁₂cycloalkyl,C₂-C₁₂alkenyl, C₃-C₁₂cycloalkenyl or C₂-C₁₂alkynyl, each of which isunsubstituted or substituted one or several times by Cl, F, OR₂₁,NR₂₂R₂₃, CN, COR₂₁, COOR₂₁ or CONR₂₂R₂₃; C₇-C₁₂aralkyl or C₆-C₁₂aryl,each of which is unsubstituted or substituted one or several times byNO₂, SOR₂₁, SO₂R₂₁, SO₃R₂₁, SO₂NR₂₂R₂₃, Br, Cl, F, OR₂₁, SR₂₁, NR₂₂R₂₃,CN, COR₂₁, COOR₂₁ or CONR₂₂R₂₃;R₁₁ and R₁₂ are independently from one another H,[C₂-C₆alkylene-O]_(n)C₁-C₁₂alkyl, [C₂-C₆alkylene-NH]_(n)C₁-C₁₂alkyl,C₁-C₁₂alkyl, C₃-C₁₂cycloalkyl, C₂-C₁₂alkenyl, C₃-C₁₂cycloalkenyl orC₂-C₁₂alkynyl, each of which is unsubstituted or substituted one orseveral times by Cl, F, OR₂₁, NR₂₂R₂₃, CN, COR₂₁, COOR₂₁ or CONR₂₂R₂₃;C₇-C₁₂aralkyl or C₆-C₁₂aryl, each of which is unsubstituted orsubstituted one or several times by NO₂, SOR₂₁, SO₂R₂₁, SO₃R₂₁,SO₂NR₂₂R₂₃, Br, Cl, F, OR₂₁, SR₂₁, NR₂₂R₂₃, CN, COR₂₁, COOR₂₁ orCONR₂₂R₂₃; orNR₁₁R₁₂ is a 5-, 6- or 7-membered, saturated, unsaturated or aromatic,heterocyclic N-radical comprising C, N, O and/or S atoms, whichheterocyclic N-radical may optionally be annellated with a cyclohexane,cyclohexene or benzene ring and is unsubstituted or substituted one orseveral times by oxo, hydroxy, C₁-C₁₂alkoxy, thiono and/or R₁₀, two ormore R₁₀ being identical or different from each other, and whichannellated benzene ring is unsubstituted or substituted by NO₂, SOR₂₁,SO₂R₂₁, SO₃R₂₁, SO₂NR₂₂R₂₃, Br, Cl, F, OR₂₁, NR₂₂R₂₃, CN, COR₂₁, COOR₂₁or CONR₂₂R₂₃;R₁₃, R₁₄ and R₁₅ have independently from R₇, R₈ and R₉ the samedefinition as R₇, R₈ and R₉, preferably R₁₃, R₁₄ and R₁₅ are eachidentical to R₇, R₈ and R₉, respectively; or R₁₃ is a direct bond from Cin position 1 or 2 of the anthraquinone substructure to R₁₆;R₁₆, R₁₇, R₁₈, R₁₉ and R₂₀ have independently from R₁, R₂, R₃, R₄ and R₅the same definition as R₁, R₂, R₃, R₄ and R₅, preferably R₁₆, R₁₇, R₁₈,R₁₉ and R₂₀ are each identical to R₁, R₂, R₃, R₄ and R₅, respectively;R₂₁, R₂₂ and R₂₃ are independently of one another H;[C₂-C₆alkylene-O]_(n)C₁-C₁₂alkyl, [C₂-C₆alkylene-NH]_(n)C₁-C₁₂alkyl orC₁-C₁₂alkyl which is unsubstituted or substituted one or several timesby F, oxo, OH, OC₁-C₆alkyl, NH₂, NHC₁-C₆alkyl, N(C₁-C₆alkyl)₂, COOH,COOC₁-C₆alkyl, CONHC₁-C₆alkyl, CON(C₁-C₆alkyl)₂ or CN; and n is aninteger 1, 2, 3, 4 or 5.

Substituted several times is to be understood as from two to all H atomsof a hydrocarbon radical being substituted. Fully substituted alkylradicals are for example trifluoromethyl, 2,2,2-trifluoroethyl-1,heptafluoropropyl or perfluorobutyl.

C₁-C₁₂Alkyl is, for example, methyl, ethyl, n-propyl, isopropyl,n-butyl, sec-butyl, isobutyl, tert-butyl, 2-methyl-butyl, n-pentyl,2-pentyl, 3-pentyl, 2,2-dimethylpropyl, n-hexyl, heptyl, n-octyl,1,1,3,3-tetramethylbutyl, 2-ethylhexyl, nonyl, decyl, undecyl ordodecyl.

C₃-C₁₂Cycloalkyl is, for example, cyclopropyl, cyclopropyl-methyl,cyclobutyl, cyclopentyl, cyclohexyl, cyclohexyl-methyl,trimethylcyclohexyl, thujyl, norbornyl, bornyl, norcaryl, caryl,menthyl, norpinyl, pinyl, 1-adamantyl or 2-adamantyl.

C₂-C₁₂Alkenyl is, for example, vinyl, allyl, 2-propen-2-yl,2-buten-1-yl, 3-buten-1-yl, 1,3-butadien-2-yl, 2-penten-1-yl,3-penten-2-yl, 2-methyl-1-buten-3-yl, 2-methyl-3-buten-2-yl,3-methyl-2-buten-1-yl, 1,4-pentadien-3-yl, or any desired isomer ofhexenyl, octenyl, nonenyl, decenyl or dodecenyl.

C₃-C₁₂Cycloalkenyl is, for example, 2-cyclobuten-1-yl,2-cyclopenten-1-yl, 2-cyclohexen-1-yl, 3-cyclohexen-1-yl,2,4-cyclohexadien-1-yl, 1-p-menthen-8-yl, 4(110)-thujen-10-yl,2-norbornen-1-yl, 2,5-norbornadiene-1-yl,7,7-dimethyl-2,4-norcaradien-3-yl or camphenyl.

C₂-C₁₂Alkynyl is, for example, 1-propyn-3-yl, 1-butyn-4-yl,1-pentyn-5-yl, 2-methyl-3-butyn-2-yl, 1,4-pentadiyn-3-yl,1,3-pentadiyn-5-yl, 1-hexyn-6-yl, cis-3-methyl-2-penten-4-yn-1-yl,trans-3-methyl-2-penten-4-yn-1-yl, 1,3-hexadiyn-5-yl, 1-octyn-8-yl,1-nonyn-9-yl, 1-decyn-10-yl or 1-dodecyn-12-yl.

C₇-C₁₂Aralkyl is, for example, benzyl, 2-benzyl-2-propyl,β-phenyl-ethyl, 9-fluorenyl, α,α-dimethylbenzyl, ω-phenyl-butyl,ω-phenyl-pentyl or ω-phenyl-hexyl. When C₇-C₁₂aralkyl is substituted,either the alkyl moiety or the aryl moiety of the aralkyl group can besubstituted.

C₆-C₁₂Aryl is, for example, phenyl, naphthyl or 1-biphenyl.

Halogen is for example F, Cl, Br or J, preferably F on alkyl and Cl orBr on aryl. Heterocyclic groups are for example

Preferably, one or two of R₁, R₂ and R₃ are H, and R₄ and R₅ are both H.More preferably, one of R₁, R₂ and R₃ is SOR₁₀, SO₂R₁₀, SO₃R₁₀,SO₂NR₁₁R₁₂, CN, COR₁₀, COOR₁₀ or CONR₁₁R₁₂, particularly preferablyCONR₁₁R₁₂ or SO₂NR₁₁R₁₂. Preferably, R₆, R₇, R₈, R₉, R₁₃, R₁₄ and R₁₅are SO₃R₁₀, SO₂NR₁₁R₁₂, NO₂, C₁-C₁₂alkyl, Cl, F or H, particularlypreferably SO₂NR₁₁R₁₂ or H.

Independently of or in combination with above preferences, R₁₀, R₁₁ orR₁₂ preferably comprise a hydroxy group, for example 1, 2 or 3 hydroxygroups.

Suitable compounds of formula (I) or (II) are for example

The compounds of formula (I) or (II) are suitably prepared for exampleby reaction of 1- or 2-halogenated anthraquinones with thiophenolderivatives. They generally exhibit an unusual thermal behaviour, whichindicates liquid crystalline properties (Liquid Crystals 27/8, 1075-1085[2000]).

The pigment can be an inorganic pigment or preferably an organicpigment. Organic pigments comprise for example, but not exclusively,anthanthrone, anthrapyrimidine, aminoanthraquinone, azo such as monoazo,disazo, β-naphthol, naphthol AS, laked azo, azocondensation,benzimidazolone or metal complexes such as metal-complex azo,azomethine, basic dye complex, diketopyrrolopyrrole, dioxazine,flavanthrone, hydroxyanthraquinone, indanthrone, indigo, isoindoline,isoindolinone, isoviolanthrone, nitro, phthalocyanine, perinone,perylene, pteridine, pyranthrone, quinacridone, quinoline,quinophthalone, thioindigo and triaryl-carbonium pigments. Mixtures ofpigments may also be used. For further details as to all those organicpigments, reference is made to Industrial Organic Pigments, W. Herbst,K. Hunger, 2nd edition, VCH Verlagsgesellschaft, Weinheim, 1997.

Pigments useful in combination with compounds of formulae (I) or (II)are, in particular, Colour Index Pigment Yellow 3, 7, 12, 13, 14, 17,24, 34, 42, 53, 62, 74, 83, 93, 95, 108, 109, 110, 111, 119, 123, 128,129, 138, 139, 147, 150, 164, 168, 173, 174, 180, 184, 188, 191, 191:1,191:2, 193, 199, Pigment Orange 5, 13, 16, 34, 40, 43, 48, 49, 51, 61,64, 71, 73, Pigment Red 2, 4, 5, 23, 48:1, 48:2, 48:3, 48:4, 52:2, 53:1,57, 57:1, 88, 89, 101, 104, 112, 122, 144, 146, 149, 166, 168, 177, 178,179, 181, 184, 190, 192, 194, 202, 204, 206, 207, 209, 214, 216, 220,221, 222, 224, 226, 254, 255, 262, 264, 270, 272, 282, 283, PigmentBrown 23, 24, 33, 42, 43, 44, Pigment Violet 19, 23, 29, 31, 37, 42,Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 25, 26, 28, 29, 60,64, 66, 80, Pigment Green 7, 17, 36, 37, 50,3,6-di(3′-cyano-phenyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione,3-phenyl-6-(4′-tert-butyl-phenyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dioneor Vat Red 74.

Especially preferred are pigments, the visible light absorption maximaof which are in the range from 400 to 500 nm and/or from 600 to 700 nm.The visible light range is from 400 to 700 nm. Most preferred pigmentsare green pigments, in particular halogenated phthalocyanine pigments,especially Colour Index Pigment Green 7, 17, 36 and/or 37. However, itis also suitable to use pigments, the visible light absorption maxima ofwhich are in the range from 500 to 570 nm, in which case the hue angle hof the red pigment is shifted to higher values (CIE-L*C*h colour space).

The instant composition preferably further comprises a photoresist asdescribed below, for example a photoinitiator and a polymerisablemonomer.

Thus, the invention further pertains to a composition comprising from0.1 to 70% by weight of a colourant comprising a pigment of averageparticle size from 10 to 200 nm and a compound of formula (I) or (II) ina weight ratio of from 99:1 to 10:90, preferably a weight ratio of from95:5 to 30:70, and a liquid medium comprising a binder or apolymerisable compound.

The 1- or 2-phenylthio-anthraquinone dye can be used as a pure compound,or optionally as a mixture of several 1- and/or2-phenylthio-anthraquinone dyes of different structures, for examplemixtures of isomers or homologues. Pigment mixtures can also be usedinstead of a pure pigment. Depending on its solubility in the liquidused for dispersing the pigment, the 1- or 2-phenylthio-anthraquinonedye may dissolve partially or completely therein upon dispersion.

Some compounds of formula (I) or (II) are particularly preferred andnovel.

Thus, the invention also relates to a compound of formula (I), whereinat least one of R₁, R₂ and R₃ is SOR₁₀, SO₂R₁₀, SO₃R₁₀, SO₂NR₁₁R₁₂, CN,COR₁₀, COOR₁₀ or CONR₁₁R₁₂, or at least one of R₆, R₇, R₈ and R₉ isSO₂NR₁₁R₁₂, with the proviso that the compound is not of formula

or a compound of formula (II), wherein at least one of R₁, R₂ and R₃ isSOR₁₀, SO₂R₁₀, SO₃R₁₀, SO₂NR₁₁R₁₂, CN, COR₁₀, COOR₁₀ or CONR₁₁R₁₂, or atleast one of R₆, R₇, R₈ and R₉ is SO₂NR₁₁R₁₂, with the proviso that thecompound is not of formula

Preferred are compounds substituted by SO₂NR₁₁R₁₂, wherein R₁, R₂, R₃,R₆, R₇, R₈ and R₉ are not SO₂NH₂.

The invention also relates to a compound of formula

wherein at least one of R₁, R₂ and R₃ is SOR₁₀, SO₂R₁₀, SO₃R₁₀,SO₂NR₁₁R₁₂, CN or COR₁₀, or at least one of R₇, R₈ and R₉ is SO₂NR₁₁R₁₂,with the proviso that R₃ is not SO₂NH₂. In formulae (III) or (IV),preferably R₁, R₂, R₇, R₈ and R₉ are not SO₂NH₂.

The compounds of formulae (I), (II), (III) and (IV) can also be used forany known colouring purpose, such as for example as solvent or dispersedyes on textiles, paper or other materials, or as colourants in printinginks, plastics and coatings.

A preferred application is the use of a compound of formula (I), (II),(III) or (IV), for enhancing or modifying the colour of high molecularweight organic materials comprising pigments.

High molecular weight organic materials are of natural or syntheticorigin (e.g. polymers) and have usually a molecular weight usually inthe range from 10³ to 10⁸ g/mol. They can be in the form of fibres,surface-coating compositions (including special-effect finishes,including those for the automotive sector) and printing inks, orpreferably also in so-called resists (for example for colour filters) oras toners. Such uses will be so obvious to the person skilled in the artthat it is possible to dispense with listing them here. They are alsodisclosed in numerous patent specifications and technical works, forexample “Industrielle Organische Pigmente” (W. Herbst+K. Hunger, VCHWeinheim/N.Y., new editions continually published in German andEnglish).

The total amount of colourants, including the compounds of formulae (I),(II), (III) and (IV) as well as the pigments, is adequately from 0.01 to75% by weight, based on the total weight of colourants and highmolecular weight organic material. In the coloured high molecular weightorganic material, for example the pixels of a patterned colour filter,the compounds of formulae (I), (II), (III) or (IV) and the pigments aresuitably in a weight ratio of from 99:1 to 10:90, preferably a weightratio of from 95:5 to 30:70.

The 1-phenyl-anthraquinone dye of formula (I) or the2-phenyl-anthraquinone dye of formula (II) can be used together with aphotoresist for producing patterned colour filters, either as the onlycolourant or in combination with customary other colourants (dyes orpigments such as disclosed above), especially with halogenated copperphthalocyanine.

Accordingly, the invention also pertains to a colour filter comprising atransparent substrate and one layer or multiple layers thereon, at leastone layer being a patterned layer, the pattern of which comprises acompound of formula (I), (II), (III) or (IV) and preferably a pigment.Preferably, the pigment and the compound of formula (I), (II), (III) or(IV) are comprised together in the pattern of the same layer. However,it is also possible the compound of formula (I), (II), (III) or (IV) andthe pigment to be in two different layers exhibiting the same patternand superposed so that their coloured areas match the same pixels,preferably adjacent layers.

The number of layers in a multi-layered structure is irrelevant for thepurpose of the invention. Generally, a multi-layered structure comprisesfrom 2 to 25 layers, especially from 3 to 10 layers, on the substrate.The layers may be patterned, especially in the case of coloured, blackor electrically switchable layers, or uniform, especially in the case ofoptional intermediate and/or protective layers. The structure of colourfilters of different types, in all of which the instant invention issuitable, is well-known in the art.

Thus, the invention further pertains to a composition comprising from0.1 to 70% by weight of a colourant comprising a pigment of averageparticle size from 10 to 200 nm and a compound of formula (I), (II),(III) or (IV) in a weight ratio of from 99:1 to 10:90, preferably aweight ratio of from 95:5 to 30:70, and a liquid medium comprising abinder or a polymerisable compound.

The invention finally pertains to a process for manufacturing a colourfilter, wherein a composition comprising from 0.1 to 70% by weight of acolourant comprising a pigment of average particle size from 10 to 200nm and a compound of formula (I), (II), (III) or (IV) in a weight ratioof from 99:1 to 10:90, preferably a weight ratio of from 95:5 to 30:70,and a liquid medium comprising a binder or a polymerisable compound isapplied onto a transparent substrate optionally comprising patterned ornot patterned layers thereon, and the composition is dried and/or curedto give a patterned layer.

The drying, patterning and curing processes are well-known in the art,but are nevertheless described below in more detail for illustrationpurpose.

The invention in particular also pertains to the use of the instantpigment compositions in colour filters, which can themselves be used forexample in electro-optical systems such as TV screens, computer screens,cellular phone screens, navigation systems, electronic agendas, chargecoupled devices, cameras, color copiers, CMOS, liquid crystal displays,flexible displays, flat panel displays, plasma displays orelectroluminescent displays and the like. These may be, for example,active (twisted nematic) or passive (supertwisted nematic) ferroelectricdisplays or light-emitting diodes.

The colourants or colourant compositions of the invention will generallybe used in the manufacture of colour filters as a solution or dispersionin an organic solvent or water. There are several ways to manufacturethese colour filters, which follow two mainstreams:

-   -   Direct patterning during applying;    -   Patterning after applying the colourant.

Direct patterning can be obtained by several printing techniques, suchas impact (off-set, flexography, stamping, letterpress etc.) as well asnon-impact (ink jet techniques).

Other direct patterning techniques are based on lamination processes,electronic discharging processes like electro-deposition and somespecial colour proofing methods, like the so-called Chromalin™ process(DuPont).

For impact printing techniques, colourants may be dissolved or dispersedin water or organic solvents by standard de-agglomeration methods(Skandex, Dynomill, Dispermat and the like) in the presence of adispersant and a polymeric binder to produce an ink. Any dispersiontechnique known in the field, including the choice of solvent,dispersant and binder, can be used. The type of ink and its viscositydepend on the application technique and are well-known to the skilledartisan. Most usual binders, to which the invention is of course notlimited, are (meth)acrylates, epoxies, PVA, polyimids, Novolak systemsand the like as well as combinations of these polymers.

The ink dispersion then can be printed on all kind of standard printingmachines. Curing of the binder system is preferably achieved by aheating process. The three colours can be applied at once or indifferent printing steps with intermediate drying and/or curing steps,for example one colour at a time in three printing steps.

Inks for use in ink jet, for example piezo or bubble jet, can beprepared likewise. They generally contain a colourant dissolved ordispersed in water and/or one or a mixture of many hydrophilic organicsolvents in combination with a dispersant and a binder.

For ink jet printing, a standard ink jet printer can be used or adedicated printer can be built in order to optimize for example theprinting speed etc.

For lamination techniques, like thermal transfer and the like, a websystem has to be made: the colourant is dispersed in a solvent or waterwith dispersant and binder and coated on a foil and dried. Thecolourant/binder system can be patternwise or uniformly transferred to acolour filter substrate with the help of energy (UV, IR, heat, pressureetc.). Depending on the technique used, the colourant for example may betransferred alone (dye diffusion or sublimation transfer), or thecolourant dispersion may be entirely transferred including the binder(wax transfer).

For electrodeposition, the colourant has to be dispersed in watertogether with an ionized polymer. By means of an electrical current, theionized polymer is deionized at the anode or the cathode and, beinginsoluble then, deposited together with the pigments. This can be doneon (transparent) photo-conductors like ITO etc. which are patterned orpatternwise shielded by a photoresist.

The Chromalin™ process makes use of a photosensitive material, depositedon a colour filter substrate. The material becomes tacky upon UVexposure. The so called ‘toner’, comprising a mixture or compound ofcolourant and polymer, is distributed on the substrate and sticks on thetacky parts. This process has to be done three to four times for R, G, Band eventually black.

Patterning after applying is a method based mostly on the knownphotoresist technology, wherein the colourant is dispersed in thephotoresist composition. Other methods are indirect patterning with thehelp of a separate photoresist or lamination techniques.

The colourant may be dissolved or dispersed into photoresists by anystandard method such as described above for the printing processes. Thebinder systems may also be identical. Further suitable compositions aredescribed for example in EP0654711, WO 98/45756 or WO 98/45757.

Photoresists comprise a photoinitiator and a poly-crosslinkable monomer(negative radical polymerization), a material to crosslink the polymersitself (for example a photoacid generator or the like) or a material tochemically change the solubility of the polymer in certain developingmedia. This process, however, can also be done with heat (for exampleusing thermal arrays or a NIR beam) instead of UV, in the case of somepolymers which undergo chemical changes upon heating, resulting inchanges of solubility in the mentioned developing media. Aphotoinitiator is then not needed.

The photosensitive or heat sensible material is coated on a colourfilter substrate, dried and UV (or heat) irradiated, sometimes againbaked (photoacid generators) and developed with a developing medium(mostly a base). In this last step only the non-exposed (negativesystems) or only the exposed (positive systems) parts are washed away,giving the wanted pattern. This operation has to be repeated for all thecolours used.

Photosensitive lamination techniques are using the same principle, theonly difference being the coating technique. A photosensitive system isapplied as described above, however on a web instead of a colour filtersubstrate. The foil is placed on the colour filter substrate and thephotosensitive layer is transferred with the help of heat and/orpressure.

Indirect processes, with the above mentioned polymeric binders without aphotosensitive component, make use of an extra photoresist, coated ontop of the pigmented resist. During the patterning of the photoresist,the coloured resist is patterned as well. The photoresist has to beremoved afterwards.

More details about the manufacture of colour filters can be found intext books, reviews and other scientific articles. The skilled artisanwill associate the instant invention with the use of any such knowntechnique as well.

For example, which is of course in no way limitative, substantiallycolourless methacrylic resin are commonly used in colour filters,examples thereof which are known to the skilled artisan being copolymersof aromatic methacrylates with methacrylic acid of M_(w) from 30'000 to60'000. Such resins are highly appropriated to make films byspin-coating.

The colour filters of the invention contain the colourant compositionsof the invention judiciously in a concentration of from 1 to 75% byweight, preferably from 5 to 50% by weight, with particular preferencefrom 25 to 40% by weight, based on the overall weight of the layercomprising said colourant.

The invention therefore likewise provides a colour filter comprising atransparent substrate and a layer comprising from 1 to 75% by weight,preferably from 5 to 50% by weight, with particular preference from 25to 40% by weight, based on the overall weight of the layer comprisingsaid colourant, of a colourant composition of the invention or theindividual components of said composition dispersed in a high molecularmass organic material. The substrate is preferably essentiallycolourless (T≧95% all over the visible range from 400 to 700 nm).

The instant printing inks or photoresists for making colour filterscontain the colourant or colourant compositions of the inventionjudiciously in a concentration of from 0.01 to 40% by weight, preferablyfrom 1 to 25% by weight, with particular preference from 5 to 10% byweight, based on the overall weight of the printing ink or photoresist.

The invention therefore likewise provides a composition for makingcolour filters comprising from 0.01 to 40% by weight, preferably from 1to 25% by weight, with particular preference from 5 to 10% by weight,based on the overall weight of the composition, of a colourant orcolourant composition of the invention dispersed therein.

This colourant composition also may additionally contain othercolourants of different structure. The additional components will shiftthe mixture's spectrum hypsochromically or bathochromically depending ontheir own hue. The skilled artisan will appreciate by himself whichcolourants can additionally be used, and in which amounts, depending onthe desired colour.

In certain cases, it is advantageous to use the inventive compositionsin mixture or in combination with other additives such as wettingagents, surfactants, defoamers, antioxidants, UV absorbers, lightstabilizers, plastisizers, or general texture improving agents and soforth. Generally such additives can be used in a concentration fromabout 0.1 to 25 percent, preferably from about 0.2 to 15% and mostpreferably from about 0.5 to 8%, by weight based on the total weight of(a), (b) and (c).

Surfactants are generally used to disperse insoluble components, such asthe copper phthalocyanine pigments. They may also be used for examplewith instant anthraquinone dyes of low solubility; however, when thewhole colourant is totally dissolved, it is generally judicious not touse surfactants, as this might lead to scattering and to a lowercontrast. Cationic, anionic, amphoteric, zwitterionic or neutralnonionic surfactants are very well known to the person skilled in theart. Suitable surfactants include for example anionic surfactants suchas alkylbenzene- or alkylnaphthalene-sulfonates, alkylsulfosuccinates ornaphthalene formaldehyde sulfonates; cationic surfactants including, forexample, quaternary salts such as benzyl tributyl ammonium chloride; ornonionic or amphoteric surfactants such as polyoxyethylene surfactantsand alkyl- or amidopropyl betaines, respectively. Most preferredsurfactant, which leads to excellent colourant dispersions andespecially highly transparent colour filters, is EFKA® 3440 (CIBASpecialty Chemicals Inc.).

Suitable texture improving agents are, for example, fatty acids such asstearic acid or behenic acid, and fatty amines such as laurylamine andstearylamine. In addition, fatty alcohols or ethoxylated fatty alcohols,polyols such as aliphatic 1,2-diols or epoxidized soy bean oil, waxes,resin acids and resin acid salts may be used for this purpose.

Suitable UV stabilizers are, for example, the known benzotriazolederivatives known under the trade name TINUVIN® or CIBA® Fast H Liquidan aryl sulfonated benzotriazol, both being products of CIBA SpecialtyChemicals Inc.

The skilled artisan will obviously recognize that there are many otherpossible applications in all fields where colourants are used, such asinks, coatings and polymers. The instant colourant or colourantcompositions will prove particularly useful alone or in combination withfine or transparent pigments. Where ever the thermal colour stability isan issue, it is worth to try resolving it by using the instantcompositions, with a reasonable expectation of much better results to beobtained. Typical examples are coil- and powder coatings, extruded orinjection moulded engineering plastics as well as melt-spun fibers, thislist self-evidently not being exhaustive.

The materials used for manufacturing colour filters according toabove-mentioned and other processes are well-known in the art.

For example, a binder may be used which is alkali-soluble, preferably alinear organic polymer that is soluble in an organic solvent anddevelopable with a weak alkali aqueous solution. As such binder used ina colour filter resist composition, which is soluble in an alkalineaqueous solution and insoluble in water, for example, a homopolymer of apolymerizable compound having one or more acid groups and one or morepolymerizable unsaturated bonds in the molecule, or a copolymer of twoor more kinds thereof, and a copolymer of one or more polymerizablecompounds having one or more unsaturated bonds copolymerizable withthese compounds and containing no acid group, can be used. Suchcompounds can be obtained by copolymerizing one or more kinds of a lowmolecular compound having one or more acid groups and one or morepolymerizable unsaturated bonds in the molecule with one or morepolymerizable compounds having one or more unsaturated bondscopolymerizable with these compounds and containing no acid group.Examples of acids groups are a —COOH group, a —SO₂NHCO— group, a —SO₃Hgroup, a phenolic hydroxy group, a —SO₂NH— group, and a —CO—NH—CO—group. Among those, a high molecular compound having a —COOH group isparticularly preferred.

Preferably, the organic polymer binder in the colour filter resistcomposition comprises an alkali soluble copolymer comprising, asaddition polymerizable monomer units, at least an unsaturated organicacid compound such as acrylic acid, methacrylic acid and the like. It ispreferred to use as a further co-monomer for the polymer binder anunsaturated organic acid ester compound such as methyl acrylate, ethyl(meth)acrylate, benzyl (meth)acrylate, styrene and the like to balanceproperties such as alkaline solubility, adhesion rigidity, chemicalresistance etc.

The organic polymer binder can for example be either a random copolymeror a block copolymer, such as described in U.S. Pat. No. 5,368,976.

Polymerizable compounds suitable for the preparation of colour filtersaccording to the invention, are also well-known in the art. They may forexample have one or more acid group and one or more polymerizableunsaturated bond in the molecule. Examples of the polymerizablecompounds having one or more —COOH groups and one or more polymerizableunsaturated bonds in a molecule are (meth)acrylic acid, 2-carboxyethyl(meth)acrylic acid, 2-carboxypropyl (meth)acrylic acid, crotonic acid,cinnamic acid, mono[2-(meth)acryloyloxyethyl]succinate,mono[2-(meth)acryloyl-oxyethyl]adipate,mono[2-(meth)acryloyloxyethyl]phthalate,mono[2-(meth)acryl-oyloxyethyl]hexahydrophthalate,mono[2-(meth)acryloyloxyethyl]maleate,mono-[2-(meth)acryloyloxypropyl]succinate,mono[2-(meth)acryloyloxypropyl]adipate,mono[2-(meth)acryloyloxypropyl]phthalate,mono[2-(meth)acryloyloxypropyl]hexahydrophthalate,mono[2-(meth)acryloyloxypropyl]maleate, mono[2-(meth)-acryloyloxybutyl]succinate, mono[2-(meth)acryloyloxybutyl]adipate,mono-[2-(meth)acryloyloxybutyl]phthalate,mono[2-(meth)acryloyloxybutyl]hexahydro-phthalate,mono[2-(meth)acryloyloxybutyl]maleate, 3-(alkylcarbamoyl)acrylic acid,α-chloroacrylic acid, maleic acid, monoesterified maleic acid, fumaricacid, itaconic acid, citraconic acid, mesaconic acid, maleic anhydride,and ω-carboxypolycapro-lactone mono(meth)acrylate.

Vinylbenzenesulfonic acid and 2-(meth)acrylamide-2-methylpropanesulfonicacid are examples of the polymerizable compounds having one or more—SO₃H groups and one or more polymerizable unsaturated bonds.

N-methylsulfonyl (meth)acrylamide, N-ethylsulfonyl (meth)acrylamide,N-phenyl-sulfonyl (meth)acrylamide, and N-(p-methylphenylsulfonyl)(meth)acrylamide are examples of the polymerizable compounds having oneor more —SO₂NHCO— groups and one or more polymerizable unsaturatedbonds.

Examples of polymerizable compounds having one or more phenolic hydroxygroups and one or more polymerizable unsaturated bonds in a moleculeinclude hydroxyphenyl (meth)acrylamide, dihydroxyphenyl(meth)acrylamide, hydroxy-phenyl-carbonyloxyethyl (meth)acrylate,hydroxyphenyloxyethyl (meth)acrylate, hydroxyphenylthioethyl(meth)acrylate, dihydroxyphenylcarbonyloxyethyl (meth)-acrylate,dihydroxyphenyloxyethyl (meth)acrylate, and dihydroxy-phenylthioethyl(meth)acrylate.

Examples of the polymerizable compound having one or more —SO₂NH— groupsand one or more polymerizable unsaturated bonds in the molecule includecompounds represented by formula (a) or (b):

CH₂═CHA₁-Y₁-A₂-SO₂—NH-A₃  (a)

CH₂═CHA₄-Y₂-A₅-NH—SO₂-A₆  (b)

wherein Y₁ and Y₂ each represents —COO—, —CONA₇-, or a single bond; A₁and A₄ each represents H or CH₃; A₂ and A₅ each representsC₁-C₁₂alkylene optionally having a substituent, cycloalkylene, arylene,or aralkylene, or C₂-C₁₂alkylene into which an ether group and athioether group are inserted, cycloalkylene, arylene, or aralkylene; A₃and A₆ each represents H, C₁-C₁₂alkyl optionally having a substituent, acycloalkyl group, an aryl group, or an aralkyl group; and A₇ representsH, C₁-C₁₂alkyl optionally having a substituent, a cycloalkyl group, anaryl group, or an aralkyl group.

The polymerizable compounds having one or more —CO—NH—CO— group and oneor more polymerizable unsaturated bond include maleimide andN-acryloyl-acryl-amide. These polymerizable compounds become the highmolecular compounds comprising a —CO—NH—CO— group, in which a ring isformed together with a primary chain by polymerization. Further, amethacrylic acid derivative and an acrylic acid derivative each having a—CO—NH—CO— group can be used as well. Such methacrylic acid derivativesand the acrylic acid derivatives include, for example, a methacrylamidederivative such as N-acetylmethacrylamide, N-propionylmethacrylamide,N-butanoylmethacrylamide, N-pentanoylmethacrylamide,N-decanoylmethacryl-amide, N-dodecanoylmethacrylamide,N-benzoylmethacrylamide, N-(p-methylbenz-oyl)methacryl-amide,N-(p-chlorobenzoyl)methacrylamide, N-(naphthyl-carbonyl)-methacrylamide,N-(phenylacetyl)-methacryl-amide, and 4-methacryloylamino-phthalimide,and an acrylamide derivative having the same substituent as these. Thesepolymerizable compounds polymerize to be compounds having a —CO—NH—CO—group in a side chain.

Examples of polymerizable compounds having one or more polymerizableunsaturated bond and containing no acid group include a compound havinga polymerizable unsaturated bond, selected from esters of (meth)acrylicacid, such as methyl (meth)acrylate, ethyl (meth)acrylate, propyl(meth)acrylate, butyl (meth)-acrylate, tetrahydrofurfuryl(meth)acrylate, benzyl (meth)acrylate, 2-ethylhexyl (meth)acrylate,hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate, hydroxybutyl(meth)acrylate, glycerol mono(meth)acrylate, dihydroxypropyl(meth)-acrylate, allyl (meth)acrylate, cyclohexyl (meth)acrylate, phenyl(meth)acrylate, methoxyphenyl (meth)acrylate, methoxyethyl(meth)acrylate, phenoxyethyl (meth)-acrylate, methoxydiethyleneglycol(meth)acrylate, methoxytriethyleneglycol (meth)-acrylate, methoxypropyl(meth)acrylate, methoxydipropyleneglycol (meth)acrylate, isobornylmeth(acrylate), dicyclopentadienyl (meth)acrylate,2-hydroxy-3-phenoxy-propyl (meth)acrylate,tricyclo[5.2.1.0^(2,6)]decan-8-yl (meth)acrylate, aminoethyl(meth)acrylate, N,N-dimethylaminoethyl (meth)acrylate, aminopropyl(meth)acryl-ate, N,N-dimethylaminopropyl (meth)acrylate, glycidyl(meth)acrylate, 2-methyl-glycidyl (meth)acrylate, 3,4-epoxybutyl(meth)acrylate, 6,7-epoxyheptyl (meth)-acrylate; vinyl aromaticcompounds, such as styrene, α-methylstyrene, vinyl-toluene,p-chlorostyrene, polychlorostyrene, fluorostyrene, bromostyrene,ethoxymethyl styrene, methoxystyrene, 4-methoxy-3-methylstyrene,dimethoxy-styrene, vinylbenzyl methyl ether, vinylbenzyl glycidyl ether,indene, 1-methyl-indene; vinyl or allyl esters, such as vinyl acetate,vinyl propionate, vinyl butylate, vinyl pivalate, vinyl benzoate, vinyltrimethylacetate, vinyl diethylacetate, vinyl borate, vinyl caproate,vinyl chloroacetate, vinyl dichloroacetate, vinyl methoxy-acetate, vinylbutoxyacetate, vinyl phenylacetate, vinyl acetate, vinyl acetoacetate,vinyl lactate, vinyl phenylbutylate, vinyl cyclohexylcarboxylate, vinylsalicylate, vinyl chlorobenzoate, vinyl tetrachlorobenzoate, vinylnaphthoate, allyl acetate, allyl propionate, allyl butylate, allylpivalate, allyl benzoate, allyl caproate, allyl stearate, allylacetoacetate, allyl lactate; vinyl or allyl ethers, such as vinyl methylether, vinyl ethyl ether, vinyl hexyl ether, vinyl octyl ether, vinylethylhexyl ether, vinyl methoxy-ethyl ether, vinyl ethoxyethyl ether,vinyl chloroethyl ether, vinyl hydroxyethyl ether, vinyl ethylbutylether, vinyl hydroxyethoxyethyl ether, vinyl dimethylaminoethyl ether,vinyl diethylaminoethyl ether, vinyl butylaminoethyl ether, vinyl benzylether, vinyl tetrahydrofurfuryl ether, vinyl phenyl ether, vinyl tolylether, vinyl chlorophenyl ether, vinyl chloroethyl ether, vinyldichlorophenyl ether, vinyl naphthyl ether, vinyl anthryl ether, allylglycidyl ether; amide type unsaturated compounds, such as(meth)acrylamide, N,N-dimethyl (meth)acrylamide, N,N-diethyl(meth)acrylamide, N,N-dibutyl (meth)acrylamide, N,N-diethylhexyl(meth)acrylamide, N,N-dicyclo-hexyl (meth)acrylamide, N,N-diphenyl(meth)acrylamide, N-methyl-N-phenyl (meth)acrylamide,N-hydroxyethyl-N-methyl (meth)acrylamide, N-methyl (meth)-acrylamide,N-ethyl (meth)acrylamide, N-propyl (meth)acrylamide, N-butyl(meth)-acrylamide, N-hydroxyethyl (meth)acrylamide, N-heptyl(meth)acrylamide, N-octyl (meth)acrylamide, N-ethyhexyl(meth)acrylamide, N-hydroxyethyl (meth)acryl-amidecyclohexyl, N-benzyl(meth)acrylamide, N-phenyl (meth)acrylamide, N-tolyl (meth)acrylamide,N-hydroxyphenyl (meth)acrylamide, N-naphthyl (meth)acryl-amide,N-phenylsulfonyl (meth)acrylamide, N-methylphenylsulfonyl(meth)acryl-amide and N-(meth)acryloylmorpholine, diacetone acrylamide,N-methylol acryl-amide, N-butoxyacrylamide; polyolefin type compounds,such as butadiene, isoprene, chloroprene and the like;(meth)acrylonitrile, methyl isopropenyl ketone, maleimide,N-phenylmaleimide, N-methylphenylmaleimide, N-methoxyphenyl-maleimide,N-cyclohexylmaleimide, N-alkylmaleimide, maleic anhydride, poly-styrenemacromonomer, polymethyl (meth)acrylate macromonomer, polybutyl(meth)acrylate macromonomer; crotonates, such as butyl crotonate, hexylcrotonate, glycerine monocrotonate; and itaconates, such as dimethylitaconate, diethyl itaconate, dibutyl itaconate; and maleates orfumarates, such as dimethyl maleate, dibutyl fumarate.

Preferable examples of copolymers are copolymers of methyl(meth)acrylate and (meth)acrylic acid, copolymers of benzyl(meth)acrylate and (meth)acrylic acid, copolymers of methyl(meth)acrylate/, ethyl (meth)acrylate and (meth)acrylic acid, copolymersof benzyl (meth)acrylate, (meth)acrylic acid and styrene, copolymers ofbenzyl (meth)acrylate, (meth)acrylic acid and 2-hydroxyethyl(meth)acrylate, copolymers of methyl (meth)acrylate/, butyl(meth)acrylate, (meth)acrylic acid and styrene, copolymers of methyl(meth)acrylate, benzyl (meth)acrylate, (metha)crylic acid andhydroxyphenyl (meth)acrylate, copolymers of methyl (meth)acrylate,(metha)crylic acid and polymethyl (meth)acrylate macromonomer,copolymers of benzyl (meth)crylate, (metha)crylic acid and polymethyl(meth)acrylate macromonomer, copolymers of tetrahydrofurfuryl(meth)acrylate, styrene and (meth)acrylic acid, copolymers of methyl(meth)acrylate, (meth)acrylic acid and polystyrene macromonomer,copolymers of benzyl (meth)acrylate, (meth)acrylic acid and polystyrenemacromonomer, copolymers of benzyl (meth)acrylate, (meth)acrylic acid,2-hydroxyethyl (meth)acrylate and polystyrene macromonomer, copolymersof benzyl (meth)acrylate, (meth)acrylic acid, 2-hydroxypropyl(meth)acrylate and polystyrene macromonomer, copolymers of benzyl(meth)acryl-ate, (meth)acrylic acid, 2-hydroxy-3-phenoxypropyl(meth)acrylate and polymethyl (meth)acrylate macromonomer, copolymers ofmethyl (meth)acrylate, (meth)acrylic acid, 2-hydroxyethyl (meth)acrylateand polystyrene macromonomer, copolymers of benzyl (meth)acrylate,(metha)crylic acid, 2-hydroxyethyl (meth)acrylate and poly-methyl(meth)acrylate macromonomer, copolymers of N-phenylmaleimide, benzyl(meth)acrylate, (metha)crylic acid and styrene, copolymers of benzyl(meth)acrylate, (meth)acrylic acid, N-phenylmaleimide,mono-[2-(meth)acryloyloxyethyl]succinate and styrene, copolymers ofallyl (meth)acrylate, (meth)acrylic acid, N-phenylmaleimide,mono-[2-(meth)acryloyloxyethyl]succinate and styrene, copolymers ofbenzyl (meth)acrylate, (meth)acrylic acid, N-phenylmaleimide, glycerolmono(meth)acrylate and styrene, copolymers of benzyl (meth)acrylate,ω-carboxy-polycaprolactone mono(meth)acrylate, (meth)acrylic acid,N-phenylmaleimide, glycerol mono(meth)acrylate and styrene, andcopolymers of benzyl (meth)acrylate, (meth)acrylic acid,N-cyclohexylmaleimide and styrene.

There can be used as well hydroxystyrene homo- or co-polymers or anovolak type phenol resin, for example, poly(hydroxystyrene) andpoly(hydroxystyrene-co-vinylcyclohexanol), a novolak resin, a cresolnovolak resin, and a halogenated phenol novolak resin. Morespecifically, it includes, for example, the methacrylic acid copolymers,the acrylic acid copolymers, the itaconic acid copolymers, the crotonicacid copolymers, the maleic anhydride co-polymers, for example, withstyrene as a co-monomer, and maleic acid copolymers, and partiallyesterified maleic acid copolymers each described in, for example,JP-B-S59/44615, JP-B-S54/34327, JP-B-S58/12577, JP-B-S54/25957,JP-A-S59/53836, JP-A-S59/71048, JP-A-S60/159743, JP-A-S60/258539,JP-A-H01/152449, JP-A-H02/199403 and JP-A-H02/199404, and whichcopolymers can be further reacted with an amine, as e.g disclosed inU.S. Pat. No. 5,650,263; further, a cellulose derivative having acarboxyl group on a side chain can be used, and particularly preferredare copolymers of benzyl (meth)acrylate and (meth)acrylic acid andcopolymers of benzyl (meth)acrylate, (meth)acrylic acid and othermonomers, for example as described in U.S. Pat. No. 4,139,391,JP-B-S59/44615, JP-A-S60/159,743 and JP-A-S60/258,539.

With respect to those having carboxylic acid groups among the aboveorganic binder polymers, it is possible to react some or all of thecarboxylic acid groups with glycidyl(meth)acrylate or anepoxy(meth)acrylate to obtain photopolymerizable organic binder polymersfor the purpose of improving the photosensitivity, coating filmstrength, the coating solvent and chemical resistance and the adhesionto the substrate. Examples are disclosed in JP-B-S50/34443 andJP-B-S50/34444, U.S. Pat. No. 5,153,095, U.S. Pat. No. 5,650,233 andU.S. Pat. No. 5,677,385, as well as by T. Kudo et al. in J. Appl. Phys.,Vol. 37 (1998), p. 3594-3603. The entire contents of all above-mentionedpatents and patent applications is enclosed herein by reference.

Among these various kinds of alkali-soluble binders, acrylic acid homo-and copolymers as well as methacrylic acid homo- and copolymers areparticularly preferred.

The weight-average molecular weight of the binders is preferably from500 to 1'000'000, e.g. from 3'000 to 1'000'000, more preferably from5'000 to 400'000.

The content of an alkali-soluble binder in the dye-containing curableresin composition is preferably from 10 to 90% by weight, morepreferably from 20 to 80% by weight, and particularly preferably from 30to 70% by weight, based on the total solid content of the dye-containingcurable resin composition.

Photopolymerisable vinyl compounds are also well known to the personskilled in the art. These monomers contain at least one ethylenic doublebond and usually have a boiling point of 100° C. or more.

Examples of suitable photopolymerisable vinyl compounds are polyethyleneglycol monoacrylate, polyethylene glycol monomethacrylate, polypropyleneglycol monoacrylate, polypropylene glycol monomethacrylate, phenoxyethylacrylate, phenoxyethyl methacrylate, polyethylene glycol diacrylate,polyethylene glycol dimethacrylate, trimethylolpropane triacrylate,trimethylolpropane triamethacrylate, neopentylglycol diacrylate,neopentylglycol dimethacrylate, pentaerythritol tri-acrylate,pentaerythritol triamethacrylate, pentaerythritol tetraacrylate,penta-erythritol tetramethacrylate, dipentaerythritol pentaacrylate,dipentaerythritol pentamethacrylate, dipentaerythritol hexaacrylate,dipentaerythritol hexameth-acrylate, tri(acryloyloxyethyl)isocyanurate.Preferred photopolymerisable vinyl compounds are dipentaerythritolpentaacrylate and dipentaerythritol pentamethacrylate.

The total content of such a photopolymerisable vinyl compound in acolourant-containing curable composition is, while it varies dependingon the material thereof, generally from 5 to 70% by weight, preferablyfrom 5 to 50% by weight, and particularly preferably from 7 to 30% byweight, based on the solid content of the composition.

Suitable photoinitiators are also well-known to the person skilled inthe art and are preferably selected from halomethyloxadiazols,halomethyl-s-triazines, 3-aryl-substituted coumarins, benzophenones,acetophenones, cyclopentadiene-benzene-iron complexes, oxime esters andoximes.

Suitable photoinitiators are described, for example, in GB-2,339,571,U.S. Pat. No. 6,485,885, GB-2,358,017, GB-2,357,293, WO-02/100903, J.Photopolym. Sci. Technol. 15, 51-57 (2002), IP. com. Journal IPCOM000012462D, 3(6), 101-109 (2003), US-2004/0102548, US-2004/0102673,PCT/EP2006/068202 and PCT/EP2006/068254.

Preferred photoinitiators are benzophenones of the formula

wherein R₂₄, R₂₅ and R₂₆ independently of one another are hydrogen,C₁-C₄-alkyl, C₁-C₄-halogenalkyl, C₁-C₄-alkoxy, chlorine orN(C₁-C₄-alkyl)₂; R₂₇ is hydrogen, C₁-C₄-alkyl, C₁-C₄-halogenalkyl,phenyl, N(C₁-C₄-alkyl)₂, COOCH₃,

and n is 2-10. Specific examples are ESACURE TZT® available fromLamberti, (a mixture of 2,4,6-trimethylbenzophenone and4-methylbenzophenone) and DAROCUR® BP (benzophenone).

Further preferred photoinitiators are alpha-hydroxy ketones,alpha-alkoxyketones or alpha-aminoketones of the formula

wherein R₂₈ is hydrogen or C₁-C₁₈-alkoxy; R₂₉ is hydrogen, C₁-C₁₈-alkyl,C₁-C₁₂hydroxyalkyl, C₁-C₁₈-alkoxy, —OCH₂CH₂—OR₃₃, morpholino,C₁-C₁₈alkyl-S—, a group H₂C═CH—, H₂C═C(CH₃)—,

a, b and c are 1-3; n is 2-10; G₃ and G₄ independently of one anotherare end groups of the polymeric structure, preferably hydrogen ormethyl; R₃₀ is hydroxy, C₁-C₁₆-alkoxy, morpholino, dimethylamino or—O(CH₂CH₂O)_(m)—C₁-C₁₆-alkyl; R₃₁ and R₃₂ independently of one anotherare hydrogen, C₁-C₆-alkyl, C₁-C₁₆-alkoxy or—O(CH₂CH₂O)_(m)—C₁-C₁₆-alkyl; or unsubstituted phenyl or benzyl; orphenyl or benzyl substituted by C₁-C₁₂-alkyl; or R₃₁ and R₃₂ togetherwith the carbon atom to which they are attached form a cyclohexyl ring;m is 1-20; with the proviso that R₃₀, R₃₁ and R₃₂ are not all togetherC₁-C₁₆-alkoxy or —O(CH₂CH₂O)_(m)—C₁-C₁₆-alkyl; and R₃₃ is hydrogen,

Specific examples are 1-hydroxy-cyclohexyl-phenyl-ketone, a mixture of1-hydroxy-cyclohexyl-phenyl-ketone with benzophenone, 2-methyl-1[4-(methylthio)phenyl]-2-morpholinopropan-1-one,2-benzyl-2-dimethylamino-1-(4-morpholinophenyl)-butanone-1,2-dimethylamino-2-(4-methyl-benzyl)-1-(4-morpholin-4-yl-phenyl)-butan-1-one,1-[4-(2-hydroxyethoxy)-phenyl]-2-hydroxy-2-methyl-1-propan-1-one,2,2-dimethoxy-1,2-diphenylethan-1-one,2-hydroxy-2-methyl-1-phenyl-propan-1-one,2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-benzyl]-phenyl}-2-methyl-propan-1-one,2-benzyl-1-(3,4-dimethoxy-phenyl)-2-dimethylamino-butan-1-one,2-hydroxy-1-{4-[4-(2-hydroxy-2-methyl-propionyl)-phenoxy]-phenyl}-2-methyl-propan-1-one,

ESACURE® KIP provided by Fratelli Lamberti and2-hydroxy-1-{1-[4-(2-hydroxy-2-methyl-propionyl)-phenyl]-1,3,3-trimethyl-indan-5-yl}-2-methyl-propan-1-one.

Further preferred photoinitiators are acylphosphine oxides of theformula

wherein R₃₄ and R₃₅ independently of one another are unsubstitutedC₁-C₂₀-alkyl, cyclohexyl, cyclopentyl, phenyl, naphthyl or biphenylyl;or C₁-C₂₀-alkyl, cyclohexyl, cyclopentyl, phenyl, naphthyl or biphenylylsubstituted by halogen, C₁-C₁₂-alkyl, C₁-C₁₂-alkoxy, C₁-C₁₂alkylthio orNR₃₇R₃₈, or R₃₄ and R₃₅ are independently of one another —(CO)R₃₆; R₃₇and R₃₈ independently of one another are hydrogen, unsubstitutedC₁-C₁₂-alkyl or C₁-C₁₂-alkyl substituted by OH or SH wherein the alkylchain may be interrupted by one to four oxygen atoms; or R₃₇ and R₃₈independently of one another are C₂-C₁₂-alkenyl, cyclopentyl,cyclohexyl, benzyl or phenyl; R₃₆ is unsubstituted cyclohexyl,cyclopentyl, phenyl, naphthyl or biphenylyl, or cyclohexyl, cyclopentyl,phenyl, naphthyl or biphenylyl substituted by halogen, C₁-C₄-alkyland/or C₁-C₄-alkoxy; or R₃₆ is a 5- or 6-membered heterocyclic ringhaving an S atom or N atom. Specific examples thereof arebis(2,4,6-trimethyl-benzoyl)-phenylphosphine oxide,bis(2,4,6-trimethylbenzoyl)-phenyl-ethoxy-phosphine oxide,2,4,6-trimethylbenzoyl-diphenyl-phosphine oxide andbis(2,6-dimethoxybenzoyl)-2,4,4-trimethylpentylphosphine oxide.

Further preferred photoinitiators are titanocenes of the formula

wherein R₃₉ and R₄₀ independently of one another are cyclopentadienyloptionally mono-, di-, or tri-substituted by C₁-C₁₈-alkyl,C₁-C₁₈-alkoxy, cyclopentyl, cyclohexyl or halogen; R₄₁ and R₄₂ arephenyl having at least one F or CF₃ substituent in ortho position to theTi—C bond and having at least a further substituent which isunsubstituted pyrrolinyl or polyoxaalkyl or which is pyrrolinyl orpolyoxaalkyl substituted by one or two C₁-C₁₂-alkyl,di(C₁-C₁₂-alkyl)aminomethyl, morpholinomethyl, C₂-C₄-alkenyl,methoxymethyl, ethoxymethyl, trimethylsilyl, formyl, methoxy or phenyl;or R₄₁ and R₄₂ are

G₅ is O, S, or NR₄₆; R₄₃, R₄₄ and R₄₅ independently of one another arehydrogen, halogen, C₂-C₁₂-alkenyl, C₁-C₁₂alkoxy, C₂-C₁₂-alkoxyinterrupted by one to four oxygen atoms, cyclohexyloxy, cyclopentyloxy,phenoxy, benzyloxy, unsubstituted phenyl or biphenyl or phenyl orbiphenyl substituted by C₁-C₄-alkoxy, halogen, phenylthio orC₁-C₄-alkylthio, with the proviso that R₄₃ and R₄₅ are not both hydrogenand that, with respect to the residue

at least one substituent R₄₃ or R₄₅ is C₁-C₁₂alkoxy or C₁-C₁₂alkoxyinterrupted by one to four oxygen atoms, cyclohexyl-oxy, cyclopentyloxy,phenoxy or benzyloxy; and R₄₆ is C₁-C₈alkyl, phenyl or cyclophenyl.Specific examples thereof arebis(η5-2,4-cyclopentadien-1-yl)-bis(2,6-difluoro-3-(1H-pyrrol-1-yl)-phenyl)-titaniumandbis(2,6-difluorophenyl)-bis[(1,2,3,4,5-η)-1-methyl-2,4-cyclopentadien-1-yl]-titanium.

Further preferred photoinitiators are phenylglyoxalates of the formula

wherein R₄₇ is H, C₁-C₁₂-alkyl or

R₄₈, R₄₉, R₅₀, R₅₁ and R₅₂ independently of one another are hydrogen,unsubstituted C₁-C₁₂-alkyl or C₁-C₁₂-alkyl substituted by OH,C₁-C₄-alkoxy, phenyl, naphthyl, halogen or CN; wherein the alkyl chainoptionally is interrupted by one or more oxygen atoms; or R₄₈, R₄₉, R₅₀,R₅₁ and R₅₂ independently of one another are C₁-C₄-alkoxy,C₁-C₄-alkylthio or NR₃₇R₃₈; R₃₇ and R₃₈ independently of one another arehydrogen, unsubstituted C₁-C₁₂-alkyl or C₁-C₁₂-alkyl substituted by OHor SH wherein the alkyl chain optionally is interrupted by one to fouroxygen atoms; or R₃₇ and R₃₈ independently of one another areC₂-C₁₂-alkenyl, cyclopentyl, cyclohexyl, benzyl or phenyl; and Y₁ isC₁-C₁₂-alkylene optionally interrupted by one or more oxygen atoms. Aspecific example thereof is oxo-phenyl-acetic acid2-[2-(2-oxo-2-phenyl-acetoxy)-ethoxy]-ethyl ester.

Further preferred photoinitiators are oxime esters of the formula

wherein z is 0 or 1; R₅₃ is hydrogen, C₃-C₈cycloalkyl; C₁-C₁₂alkyl whichis unsubstituted or substituted by one or more halogen, phenyl and/orCN; or R₅₃ is C₂-C₅alkenyl; phenyl which is unsubstituted or substitutedby one or more C₁-C₆alkyl, halogen, CN, OR₅₆, SR₅₇ and/or NR₅₈R₅₉; orR₅₃ is C₁-C₈-alkoxy, benzyloxy; or phenoxy which is unsubstituted orsubstituted by one or more C₁-C₆alkyl and/or halogen; R₅₄ is phenyl,naphthyl, benzoyl or naphthoyl, each of which is substituted 1 to 7times by halogen, C₁-C₁₂alkyl, C₃-C₈cycloalkyl, benzyl, phenoxycarbonyl,C₂-C₁₂alkoxycarbonyl, OR₅₆, SR₆₀ SOR₅₇, SO₂R₅₇ and/or NR₅₈R₅₉, whereinthe substituents OR₅₆, SR₅₇ and NR₅₈R₅₉ optionally form 5- or 6-memberedrings via the radicals R₅₆, R₅₇, R₅₈ and/or R₅₉ with furthersubstituents on the phenyl or naphthyl ring; or each of which issubstituted by phenyl or by phenyl which is substituted by one or moreOR₅₆, SR₅₇ and/or NR₅₈R₅₉; or R₅₄ is thioxanthylor

R₅₅ is hydrogen; unsubstituted C₁-C₂₀alkyl or C₁-C₂₀alkyl substituted byone or more halogen, OR₅₆, phenyl; or is C₃-C₈cycloalkyl; phenyl whichis unsubstituted or substituted by one or more C₁-C₆alkyl, phenyl,halogen, OR₅₆, SR₅₇ and/or NR₅₈R₅₉; or is C₂-C₂₀alkanoyl or benzoylwhich is unsubstituted or substituted by one or more C₁-C₆alkyl, phenyl,OR₅₆, SR₅₇ and/or NR₅₈R₅₉; or is C₂-C₁₂alkoxycarbonyl, phenoxycarbonyl,CN, —CONR₅₈R₅₉, NO₂, C₁-C₄haloalkyl, S(O)_(y)—C₁-C₆alkyl orS(O)_(y)-phenyl; y is 1 or 2; R₅₆ and R₅₇ independently of one anotherare hydrogen, C₁-C₂₀alkyl, C₂-C₁₂alkenyl, C₃-C₈cycloalkyl,phenyl-C₁-C₃alkyl; or are C₁-C₈alkyl which is substituted by —OH, —SH,—CN, C₁-C₈alkanoyl, benzoyl, which is unsubstituted or substituted byone or more C₁-C₆alkyl, halogen, —OH, C₁-C₄alkoxy or C₁-C₄alkylsulfanyl;or are phenyl or naphthyl, each of which is unsubstituted or substitutedby halogen, C₁-C₁₂alkyl, C₁-C₁₂alkoxy, phenyl-C₁-C₃alkyloxy, phenoxy,C₁-C₁₂alkylsulfanyl, phenylsulfanyl, —N(C₁-C₁₂alkyl)₂, diphenylamino;R₅₈ and R₅₉ independently of one another are independently of each otherare hydrogen, C₁-C₂₀alkyl, C₂-C₄hydroxyalkyl, C₂-C₁₀alkoxyalkyl,C₂-C₅alkenyl, C₃-C₈cycloalkyl, phenyl-C₁-C₃alkyl, C₁-C₈alkanoyl,C₃-C₁₂alkenoyl, benzoyl; or are phenyl or naphthyl, each of which isunsubstituted or substituted by C₁-C₁₂alkyl, benzoyl or C₁-C₁₂alkoxy; orR₅₈ and R₅₉ together are C₂-C₆alkylene optionally interrupted by —O— or—NR₅₆— and/or optionally substituted by hydroxyl, C₁-C₄alkoxy,C₂-C₄alkanoyloxy or benzoyloxy; R₆₁ is C₁-C₁₂alkyl, phenyl,C₁-C₁₂alkylphenyl or 2-(2′-tetrahydrofuryl)-phenyl. Specific examplesthereof are 1,2-octanedione 1-[4-(phenylthio)phenyl]-2-(O-benzoyloxime),ethanone1-[9-ethyl-6-(2-methylbenzoyl)-9H-carbazol-3-yl]-1-(O-acetyloxime) and9H-thioxanthene-2-carboxaldehyde 9-oxo-2-(O-acetyloxime).

A further example of a photoinitiator is Esacure® 1001 available fromLamberti:1-[4-(4-benzoylphenylsulfanyl)phenyl]-2-methyl-2-(4-methylphenysulfonyl)propan-1-one

The most preferred photoinitiators are the following compounds:

The photoinitiator may be used in combination with a sensitizer and/or aphotostabiliser.

The total content of the photoinitiator is preferably from 0.01 to 10%by weight, preferably from 0.05 to 8% by weight, and particularlypreferably from 1 to 5% by weight, based on the solid content of thecomposition.

Upon preparation of the dye-containing curable composition, a solvent isgenerally used. The solvent is not particularly limited as far as itsatisfies solubility to the respective components and coating propertyof the dye-containing curable composition and it is preferably selectedunder particular consideration of the solubility of the alkali-solublebinder, the coating property and the safety.

Suitable solvents include esters, e.g. ethyl acetate, butyl acetate,butyl butyrate and methyl methoxyacetate, ether esters such as1-methoxy-2-propyl-acetate (PGMEA), 2-methoxy-1-propyl-acetate,methylcellosolve acetate, diethylene glycol dimethyl ether,butylcarbitol acetate and polyethylene glycol methyl ether acrylate(PEGMEA), ethers, e.g. tetrahydrofuran, ketones, e.g. 2-butanone,cyclopentanone and cyclohexanone, and aromatic hydrocarbons such astoluene and xylene.

The instant new anthraquinone colourants and colourant compositions arewell-dispersible in solvents and/or binders and lead to excellentrheology and storage stability of the resulting compositions. Colourfilters made manufactured from these compositions exhibit outstandinghue, resolution, contrast and transparency in the spectral range above500 nm, especially from 500 to 550 nm in combination with phthalocyaninegreen pigments, together with excellent general properties such as lightand thermal stability.

The examples which follow illustrate the invention, without limiting it(“%” are by weight where not otherwise specified):

EXAMPLE 1

45 g Thiophenol are added dropwise to a suspension of 100 g1-chloro-anthraquinone and 63 g potassium carbonate in 150 mlethoxyethanol at 23° C. under stirring. The reaction is stronglyexotherm and addition must be performed very slowly, and subsequentaddition of solvent improves fluidity and stirring of the reactionmixture. After heating at 120° C. for 3½ hours and subsequent cooling to23° C., the mixture is filtered on glass (porosity 3) to afford apresscake which is washed with 1 l of methanol. The presscake is in turnsuspended in 1 l water at 50° C. and again filtered on a glass filter(porosity 3). Further washing of the presscake with warm water (4 l)affords a filtrate of neutral pH. The presscake is finally dried at 60°C./5·10³ Pa for 12 hours to provide 124.1 g of powdery orange1-phenylsulfanyl-anthraquinone of formula

HPLC(CH₃CN): purity 94% with λ_(max) at 300 nm and 426 nm (PVC: 432 nm);

ESI-LC-MS: M=316 g/mol and 424 g/mol (traces ofbis-phenylsulfanyl-anthraquinone) by negative ionisation;

Analysis: C H N O S [%] 75.36 3.82 — 10.14 10.16 calc.: 75.93 3.82 0.0010.11 10.13

EXAMPLE 2

10 g 1-Phenylsulfanyl-anthraquinone are added in portions at 23° C. to100 ml of chlorosulfonic acid. The thus obtained reaction mixture isstirred for 4 hours, then carefully poured into an ice-sodium chloridebath. The resulting suspension is filtered on glass, thoroughly washedwith water and suspended in 150 ml of tetrahydrofuran. Drop-wiseaddition of an excess of ethanolamine (6 g) results in a red-orangesolution which is stirred for 12 hours. The reaction mixture is thenpoured on ice and the resulting yellow suspension filtered on glass. Thecollected powder is dried at 50° C./5·10³ Pa for 5 hours. The dry powderis dissolved in 100 ml of acetone/hexane (9:1) and heated to 40° C. Thesolution is then filtered hot and the press-cake is washed with acetone.The resulting powder is finally dried at 60° C./5·10³ Pa for 15 hours,to afford 9.2 g of the product of formula

HPLC (THF): purity 94.5% with λ_(max) at 306 nm and 422 nm;

Melting point: 186° C. (by DSC, 30-300° C. at 10° C./min);

ESI-LC-MS: M=439 g/mol by negative ionisation;

NMR (DMSO-d₆+D₂O): 8.13 (t, Ar—H, 2H), 7.95 (d, Ar—H, 1H), 7.83-7.90 (m,Ar—H, 4H), 7.74 (d, Ar—H, 2H), 7.55 (t, Ar—H, 1H), 7.04 (d, Ar—H, 1H),3.39 (t, —CH₂—, 2H), 2.88 (t, —CH₂—, 2H);

Analysis: C H N O S [%] 60.36 4.36 3.10 18.60 14.36 calc.: 60.12 3.903.19 18.20 14.59

EXAMPLE 3

It is proceeded as in example 2, with the difference that2-(2-hydroxy-ethylamino)-ethanol is used instead of 2-amino-ethanol inthe second step. The product of following formula is obtained:

HPLC (THF): purity 96.7% with λ_(max) at 307 nm and 422 nm.

Differential Scanning Calorimetry (30-300° C. at 10° C./min): 158° C.(endotherm), 161° C. (exotherm) and 186° C. (endotherm).

ESI-LC-MS: M=483 g/mol by negative ionisation.

NMR (DMSO-d₆): 8.10-8.18 (m, Ar—H, 2H), 7.96 (d, Ar—H, 1H), 7.80-7.91(m, Ar—H, 4H), 7.75 (d, Ar—H, 2H), 7.61 (t, Ar—H, 1H), 7.05 (d, Ar—H,1H), 4.75 (t, —OH, 2H), 3.45-3.50 (m, —CH₂—, 4H), 3.16-3.20 (m, —CH₂—,4H);

Analysis: C H N O S [%] 59.79 4.43 2.83 19.95 13.21 calc.: 59.61 4.382.90 19.85 13.26Surprisingly, different pattern in the Differential Scanning Calorimetryspectrum are obtained, depending on the isolation method of the product,involving precipitation from various organic solvents. For example, theproduct is dissolved in hot 2-butoxyethanol, slowly diluted with tolueneat 100° C. and after cooling down to 60° C., then slowly precipitated byaddition of hexane (95.7% purity by HPLC):

DSC (30-300° C. at 10° C./min): 188° C. (endotherm), but the sharpinflexions 158° C. (endotherm) and 161° C. (exotherm) observedpreviously are not present in this spectrum.

EXAMPLE 4

It is proceeded as in example 2, with the difference that2-(2-amino-ethoxy)-ethanol is used instead of 2-amino-ethanol in thesecond step. The product of following formula is obtained:

HPLC (THF): purity 89.8% with λ_(max) at 306 nm and 422 nm;

Melting point: 153° C. (Differential Scanning Calorimetry, 30-300.0° C.at 10° C./min);

ESI-LC-MS: M=483 g/mol by negative ionisation;

NMR (DMSO-d₆+D₂O): 8.13-8.22 (m, Ar—H, 2H), 7.99 (d, Ar—H, 1H),7.86-7.95 (m, Ar—H, 4H), 7.80 (d, Ar—H, 2H), 7.64 (t, Ar—H, 1H), 7.09(d, Ar—H, 1H), 3.35-3.50 (m, —CH₂—, 4H), 3.30-3.35 (m, —CH₂—, 2H), 2.99(t, —CH₂—, 2H);

Analysis: C H N O S [%] 59.31 4.52 2.79 19.98 12.99 calc.: 59.61 4.382.90 19.85 13.26

EXAMPLE 5

It is proceeded as in example 2, with the difference that3-amino-propane-1,2-diol is used instead of 2-amino-ethanol in thesecond step. The product of following formula is obtained:

HPLC (THF): purity 91.5% with λ_(max) at 306 nm and 423 nm;

Melting point: 177° C. (Differential Scanning Calorimetry, 30-300° C. at10° C./min;

ESI-LC-MS of (5): M=469 g/mol by negative ionisation;

Analysis: C H N O S [%] 58.91 4.19 2.91 20.64 13.69 calc.: 58.84 4.082.98 20.44 13.66

EXAMPLE 6

It is proceeded as in example 2, with the difference that1-(2-hydroxy-propylamino)-propan-2-ol is used instead of 2-amino-ethanolin the second step. The product of following formula is obtained:

HPLC (THF): purity 98.1% with λ_(max) at 307 nm and 421 nm;

ESI-LC-MS: M=511 g/mol by negative ionisation;

Differential Scanning Calorimetry (30-300.0° C. at 10° C./min): 101° C.(endotherm), 106° C. (exotherm) and 193° C. (endotherm);

NMR (DMSO-d₆+D₂O): 8.15-8.30 (m, Ar—H, 2H), 8.01 (d, Ar—H, 1H),7.88-7.97 (m, Ar—H, 4H), 7.80 (d, Ar—H, 2H), 7.66 (t, Ar—H, 1H), 7.08(d, Ar—H, 1H), 3.80-4.95 (m, —CH(sp³), 2H), 2.85-3.30 (m, —N—CH₂—, 4H),1.02 (d, —CH₃, 6H).

Analysis: C H N O S [%] 59.36 5.11 2.50 20.40 12.16 calc.: 61.04 4.932.74 18.76 12.53

Examples 7-589:

Ex. R₁ R₂ R₃ R₄ R₅ R₆ R₇ 7 H H SO₂R₆R₇ H H CH₃ CH₂CH₂OH 8 H H SO₂R₆R₇ HH CH₂CH₃ CH₂CH₂OH 9 H H SO₂R₆R₇ H H H CH(CH₃)—CH₂OH 10 H H SO₂R₆R₇ H H HCH—(CH₂OH)—CH₂CH₃ 11 H H SO₂R₆R₇ H H H CH₂CH₂SH 12 H H SO₂R₆R₇ H HCH₂C₆H₅ CH₂CH₂OH 13 H H SO₂R₆R₇ H H CH₂CH₂—CH₃ CH₂CH₂OH 14 H H SO₂R₆R₇ HH H CH₂CH—(CH₃)OH 15 H H SO₂R₆R₇ H H H CH₂CH₂—CH₂OH 16 H H SO₂R₆R₇ H H HCH₂CH₂—CH₂CH₂OH 17 H H SO₂R₆R₇ H H H CH(CH₂—CH₂CH₃)—CH₂OH 18 H H SO₂R₆R₇H H CH(CH₃)₂ CH₂CH₂OH 19 H H SO₂R₆R₇ H H H CH—(CH₂OH)₂ 20 H H SO₂R₆R₇ HH H CH₂—CH(OH)—CH₂CH₃ 21 SO₂R₆R₇ H CH₃ H H H CH₂CH₂OH 22 SO₂R₆R₇ H CH₃ HH CH₂CH₂OH CH₂CH₂OH 23 SO₂R₆R₇ H CH₃ H H H CH₂CH₂O—CH₂CH₂OH 24 SO₂R₆R₇ HCH₃ H H H CH₂—CH(OH)—CH₂OH 25 SO₂R₆R₇ H CH₃ H H CH₂CH—(CH₃)OHCH₂CH—(CH₃)OH 26 SO₂R₆R₇ H CH₃ H H CH₃ CH₂CH₂OH 27 SO₂R₆R₇ H CH₃ H HCH₂CH₃ CH₂CH₂OH 28 SO₂R₆R₇ H CH₃ H H H CH(CH₃)—CH₂OH 29 SO₂R₆R₇ H CH₃ HH H CH—(CH₂OH)—CH₂CH₃ 30 SO₂R₆R₇ H CH₃ H H H CH₂CH₂SH 31 SO₂R₆R₇ H CH₃ HH CH₂C₆H₅ CH₂CH₂OH 32 SO₂R₆R₇ H CH₃ H H CH₂CH₂—CH₃ CH₂CH₂OH 33 SO₂R₆R₇ HCH₃ H H H CH₂CH—(CH₃)OH 34 SO₂R₆R₇ H CH₃ H H H CH₂CH₂—CH₂OH 35 SO₂R₆R₇ HCH₃ H H H CH₂CH₂—CH₂CH₂OH 36 SO₂R₆R₇ H CH₃ H H H CH(CH₂—CH₂CH₃)—CH₂OH 37SO₂R₆R₇ H CH₃ H H CH(CH₃)₂ CH₂CH₂OH 38 SO₂R₆R₇ H CH₃ H H H CH—(CH₂OH)₂39 SO₂R₆R₇ H CH₃ H H H CH₂—CH(OH)—CH₂CH₃ 40 SO₂R₆R₇ H CH₂CH₃ H H HCH₂CH₂OH 41 SO₂R₆R₇ H CH₂CH₃ H H CH₂CH₂OH CH₂CH₂OH 42 SO₂R₆R₇ H CH₂CH₃ HH H CH₂CH₂O—CH₂CH₂OH 43 SO₂R₆R₇ H CH₂CH₃ H H H CH₂—CH(OH)—CH₂OH 44SO₂R₆R₇ H CH₂CH₃ H H CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 45 SO₂R₆R₇ H CH₂CH₃ H HCH₃ CH₂CH₂OH 46 SO₂R₆R₇ H CH₂CH₃ H H CH₂CH₃ CH₂CH₂OH 47 SO₂R₆R₇ H CH₂CH₃H H H CH(CH₃)—CH₂OH 48 SO₂R₆R₇ H CH₂CH₃ H H H CH—(CH₂OH)—CH₂CH₃ 49SO₂R₆R₇ H CH₂CH₃ H H H CH₂CH₂SH 50 SO₂R₆R₇ H CH₂CH₃ H H CH₂C₆H₅ CH₂CH₂OH51 SO₂R₆R₇ H CH₂CH₃ H H CH₂CH₂—CH₃ CH₂CH₂OH 52 SO₂R₆R₇ H CH₂CH₃ H H HCH₂CH—(CH₃)OH 53 SO₂R₆R₇ H CH₂CH₃ H H H CH₂CH₂—CH₂OH 54 SO₂R₆R₇ H CH₂CH₃H H H CH₂CH₂—CH₂CH₂OH 55 SO₂R₆R₇ H CH₂CH₃ H H H CH(CH₂—CH₂CH₃)—CH₂OH 56SO₂R₆R₇ H CH₂CH₃ H H CH(CH₃)₂ CH₂CH₂OH 57 SO₂R₆R₇ H CH₂CH₃ H H HCH—(CH₂OH)₂ 58 SO₂R₆R₇ H CH₂CH₃ H H H CH₂—CH(OH)—CH₂CH₃ 59 CH₃ H SO₂R₆R₇H H H CH₂CH₂OH 60 CH₃ H SO₂R₆R₇ H H CH₂CH₂OH CH₂CH₂OH 61 CH₃ H SO₂R₆R₇ HH H CH₂CH₂O—CH₂CH₂OH 62 CH₃ H SO₂R₆R₇ H H H CH₂—CH(OH)—CH₂OH 63 CH₃ HSO₂R₆R₇ H H CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 64 CH₃ H SO₂R₆R₇ H H CH₃CH₂CH₂OH 65 CH₃ H SO₂R₆R₇ H H CH₂CH₃ CH₂CH₂OH 66 CH₃ H SO₂R₆R₇ H H HCH(CH₃)—CH₂OH 67 CH₃ H SO₂R₆R₇ H H H CH—(CH₂OH)—CH₂CH₃ 68 CH₃ H SO₂R₆R₇H H H CH₂CH₂SH 69 CH₃ H SO₂R₆R₇ H H CH₂C₆H₅ CH₂CH₂OH 70 CH₃ H SO₂R₆R₇ HH CH₂CH₂—CH₃ CH₂CH₂OH 71 CH₃ H SO₂R₆R₇ H H H CH₂CH—(CH₃)OH 72 CH₃ HSO₂R₆R₇ H H H CH₂CH₂—CH₂OH 73 CH₃ H SO₂R₆R₇ H H H CH₂CH₂—CH₂CH₂OH 74 CH₃H SO₂R₆R₇ H H H CH(CH₂—CH₂CH₃)—CH₂OH 75 CH₃ H SO₂R₆R₇ H H CH(CH₃)₂CH₂CH₂OH 76 CH₃ H SO₂R₆R₇ H H H CH—(CH₂OH)₂ 77 CH₃ H SO₂R₆R₇ H H HCH₂—CH(OH)—CH₂CH₃ 78 H CH₃ SO₂R₆R₇ H H H CH₂CH₂OH 79 H CH₃ SO₂R₆R₇ H HCH₂CH₂OH CH₂CH₂OH 80 H CH₃ SO₂R₆R₇ H H H CH₂CH₂O—CH₂CH₂OH 81 H CH₃SO₂R₆R₇ H H H CH₂—CH(OH)—CH₂OH 82 H CH₃ SO₂R₆R₇ H H CH₂CH—(CH₃)OHCH₂CH—(CH₃)OH 83 H CH₃ SO₂R₆R₇ H H CH₃ CH₂CH₂OH 84 H CH₃ SO₂R₆R₇ H HCH₂CH₃ CH₂CH₂OH 85 H CH₃ SO₂R₆R₇ H H H CH(CH₃)—CH₂OH 86 H CH₃ SO₂R₆R₇ HH H CH—(CH₂OH)—CH₂CH₃ 87 H CH₃ SO₂R₆R₇ H H H CH₂CH₂SH 88 H CH₃ SO₂R₆R₇ HH CH₂C₆H₅ CH₂CH₂OH 89 H CH₃ SO₂R₆R₇ H H CH₂CH₂—CH₃ CH₂CH₂OH 90 H CH₃SO₂R₆R₇ H H H CH₂CH—(CH₃)OH 91 H CH₃ SO₂R₆R₇ H H H CH₂CH₂—CH₂OH 92 H CH₃SO₂R₆R₇ H H H CH₂CH₂—CH₂CH₂OH 93 H CH₃ SO₂R₆R₇ H H HCH(CH₂—CH₂CH₃)—CH₂OH 94 H CH₃ SO₂R₆R₇ H H CH(CH₃)₂ CH₂CH₂OH 95 H CH₃SO₂R₆R₇ H H H CH—(CH₂OH)₂ 96 H CH₃ SO₂R₆R₇ H H H CH₂—CH(OH)—CH₂CH₃ 97SO₂R₆R₇ H OCH₃ H H H CH₂CH₂OH 98 SO₂R₆R₇ H OCH₃ H H CH₂CH₂OH CH₂CH₂OH 99SO₂R₆R₇ H OCH₃ H H H CH₂CH₂O—CH₂CH₂OH 100 SO₂R₆R₇ H OCH₃ H H HCH₂—CH(OH)—CH₂OH 101 SO₂R₆R₇ H OCH₃ H H CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 102SO₂R₆R₇ H OCH₃ H H CH₃ CH₂CH₂OH 103 SO₂R₆R₇ H OCH₃ H H CH₂CH₃ CH₂CH₂OH104 SO₂R₆R₇ H OCH₃ H H H CH(CH₃)—CH₂OH 105 SO₂R₆R₇ H OCH₃ H H HCH—(CH₂OH)—CH₂CH₃ 106 SO₂R₆R₇ H OCH₃ H H H CH₂CH₂SH 107 SO₂R₆R₇ H OCH₃ HH CH₂C₆H₅ CH₂CH₂OH 108 SO₂R₆R₇ H OCH₃ H H CH₂CH₂—CH₃ CH₂CH₂OH 109SO₂R₆R₇ H OCH₃ H H H CH₂CH₂—(CH₃)OH 110 SO₂R₆R₇ H OCH₃ H H HCH₂CH₂—CH₂OH 111 SO₂R₆R₇ H OCH₃ H H H CH₂CH₂—CH₂CH₂OH 112 SO₂R₆R₇ H OCH₃H H H CH(CH₂—CH₂CH₃)—CH₂OH 113 SO₂R₆R₇ H OCH₃ H H CH(CH₃)₂ CH₂CH₂OH 114SO₂R₆R₇ H OCH₃ H H H CH—(CH₂OH)₂ 115 SO₂R₆R₇ H OCH₃ H H HCH₂—CH(OH)—CH₂CH₃ 116 OCH₃ H SO₂R₆R₇ H H H CH₂CH₂OH 117 OCH₃ H SO₂R₆R₇ HH CH₂CH₂OH CH₂CH₂OH 118 OCH₃ H SO₂R₆R₇ H H H CH₂CH₂O—CH₂CH₂OH 119 OCH₃ HSO₂R₆R₇ H H H CH₂—CH(OH)—CH₂OH 120 OCH₃ H SO₂R₆R₇ H H CH₂CH—(CH₃)OHCH₂CH—(CH₃)OH 121 OCH₃ H SO₂R₆R₇ H H CH₃ CH₂CH₂OH 122 OCH₃ H SO₂R₆R₇ H HCH₂CH₃ CH₂CH₂OH 123 OCH₃ H SO₂R₆R₇ H H H CH(CH₃)—CH₂OH 124 OCH₃ HSO₂R₆R₇ H H H CH—(CH₂OH)—CH₂CH₃ 125 OCH₃ H SO₂R₆R₇ H H H CH₂CH₂SH 126OCH₃ H SO₂R₆R₇ H H CH₂C₆H₅ CH₂CH₂OH 127 OCH₃ H SO₂R₆R₇ H H CH₂CH₂—CH₃CH₂CH₂OH 128 OCH₃ H SO₂R₆R₇ H H H CH₂CH—(CH₃)OH 129 OCH₃ H SO₂R₆R₇ H H HCH₂CH₂—CH₂OH 130 OCH₃ H SO₂R₆R₇ H H H CH₂CH₂—CH₂CH₂OH 131 OCH₃ H SO₂R₆R₇H H H CH(CH₂—CH₂CH₃)—CH₂OH 132 OCH₃ H SO₂R₆R₇ H H CH(CH₃)₂ CH₂CH₂OH 133OCH₃ H SO₂R₆R₇ H H H CH—(CH₂OH)₂ 134 OCH₃ H SO₂R₆R₇ H H HCH₂—CH(OH)—CH₂CH₃ 135 CH(CH₃)₂ H SO₂R₆R₇ H H H CH₂CH₂OH 136 CH(CH₃)₂ HSO₂R₆R₇ H H CH₂CH₂OH CH₂CH₂OH 137 CH(CH₃)₂ H SO₂R₆R₇ H H HCH₂CH₂O—CH₂CH₂OH 138 CH(CH₃)₂ H SO₂R₆R₇ H H H CH₂—CH(OH)—CH₂OH 139CH(CH₃)₂ H SO₂R₆R₇ H H CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 140 CH(CH₃)₂ HSO₂R₆R₇ H H CH₃ CH₂CH₂OH 141 CH(CH₃)₂ H SO₂R₆R₇ H H CH₂CH₃ CH₂CH₂OH 142CH(CH₃)₂ H SO₂R₆R₇ H H H CH(CH₃)—CH₂OH 143 CH(CH₃)₂ H SO₂R₆R₇ H H HCH—(CH₂OH)—CH₂CH₃ 144 CH(CH₃)₂ H SO₂R₆R₇ H H H CH₂CH₂SH 145 CH(CH₃)₂ HSO₂R₆R₇ H H CH₂C₆H₅ CH₂CH₂OH 146 CH(CH₃)₂ H SO₂R₆R₇ H H CH₂CH₂—CH₃CH₂CH₂OH 147 CH(CH₃)₂ H SO₂R₆R₇ H H H CH₂CH—(CH₃)OH 148 CH(CH₃)₂ HSO₂R₆R₇ H H H CH₂CH₂—CH₂OH 149 CH(CH₃)₂ H SO₂R₆R₇ H H H CH₂CH₂—CH₂CH₂OH150 CH(CH₃)₂ H SO₂R₆R₇ H H H CH(CH₂—CH₂CH₃)—CH₂OH 151 CH(CH₃)₂ H SO₂R₆R₇H H CH(CH₃)₂ CH₂CH₂OH 152 CH(CH₃)₂ H SO₂R₆R₇ H H H CH—(CH₂OH)₂ 153CH(CH₃)₂ H SO₂R₆R₇ H H H CH₂—CH(OH)—CH₂CH₃ 154 CH₂CH₃ H SO₂R₆R₇ H H HCH₂CH₂OH 155 CH₂CH₃ H SO₂R₆R₇ H H CH₂CH₂OH CH₂CH₂OH 156 CH₂CH₃ H SO₂R₆R₇H H H CH₂CH₂O—CH₂CH₂OH 157 CH₂CH₃ H SO₂R₆R₇ H H H CH₂CH(OH)—CH₂OH 158CH₂CH₃ H SO₂R₆R₇ H H CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 159 CH₂CH₃ H SO₂R₆R₇ HH CH₃ CH₂CH₂OH 160 CH₂CH₃ H SO₂R₆R₇ H H CH₂CH₃ CH₂CH₂OH 161 CH₂CH₃ HSO₂R₆R₇ H H H CH(CH₃)—CH₂OH 162 CH₂CH₃ H SO₂R₆R₇ H H H CH—(CH₂OH)—CH₂CH₃163 CH₂CH₃ H SO₂R₆R₇ H H H CH₂CH₂SH 164 CH₂CH₃ H SO₂R₆R₇ H H CH₂C₆H₅CH₂CH₂OH 165 CH₂CH₃ H SO₂R₆R₇ H H CH₂CH₂—CH₃ CH₂CH₂OH 166 CH₂CH₃ HSO₂R₆R₇ H H H CH₂CH—(CH₃)OH 167 CH₂CH₃ H SO₂R₆R₇ H H H CH₂CH₂—CH₂OH 168CH₂CH₃ H SO₂R₆R₇ H H H CH₂CH₂—CH₂CH₂OH 169 CH₂CH₃ H SO₂R₆R₇ H H HCH(CH₂—CH₂CH₃)—CH₂OH 170 CH₂CH₃ H SO₂R₆R₇ H H CH(CH₃)₂ CH₂CH₂OH 171CH₂CH₃ H SO₂R₆R₇ H H H CH—(CH₂OH)₂ 172 CH₂CH₃ H SO₂R₆R₇ H H HCH₂—CH(OH)—CH₂CH₃ 173 SO₂R₆R₇ H CH₂CH₂—CH₃ H H H CH₂CH₂OH 174 SO₂R₆R₇ HCH₂CH₂—CH₃ H H CH₂CH₂OH CH₂CH₂OH 175 SO₂R₆R₇ H CH₂CH₂—CH₃ H H HCH₂CH₂O—CH₂CH₂OH 176 SO₂R₆R₇ H CH₂CH₂—CH₃ H H H CH₂—CH(OH)—CH₂OH 177SO₂R₆R₇ H CH₂CH₂—CH₃ H H CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 178 SO₂R₆R₇ HCH₂CH₂—CH₃ H H CH₃ CH₂CH₂OH 179 SO₂R₆R₇ H CH₂CH₂—CH₃ H H CH₂CH₃ CH₂CH₂OH180 SO₂R₆R₇ H CH₂CH₂—CH₃ H H H CH(CH₃)—CH₂OH 181 SO₂R₆R₇ H CH₂CH₂—CH₃ HH H CH—(CH₂OH)—CH₂CH₃ 182 SO₂R₆R₇ H CH₂CH₂—CH₃ H H H CH₂CH₂SH 183SO₂R₆R₇ H CH₂CH₂—CH₃ H H CH₂C₆H₅ CH₂CH₂OH 184 SO₂R₆R₇ H CH₂CH₂—CH₃ H HCH₂CH₂—CH₃ CH₂CH₂OH 185 SO₂R₆R₇ H CH₂CH₂—CH₃ H H H CH₂CH—(CH₃)OH 186SO₂R₆R₇ H CH₂CH₂—CH₃ H H H CH₂CH₂—CH₂OH 187 SO₂R₆R₇ H CH₂CH₂—CH₃ H H HCH₂CH₂—CH₂CH₂OH 188 SO₂R₆R₇ H CH₂CH₂—CH₃ H H H CH(CH₂—CH₂CH₃)—CH₂OH 189SO₂R₆R₇ H CH₂CH₂—CH₃ H H CH(CH₃)₂ CH₂CH₂OH 190 SO₂R₆R₇ H CH₂CH₂—CH₃ H HH CH—(CH₂OH)₂ 191 SO₂R₆R₇ H CH₂CH₂—CH₃ H H H CH₂—CH(OH)—CH₂CH₃ 192SO₂R₆R₇ H CH₂CH₂—CH₂CH₃ H H H CH₂CH₂OH 193 SO₂R₆R₇ H CH₂CH₂—CH₂CH₃ H HCH₂CH₂OH CH₂CH₂OH 194 SO₂R₆R₇ H CH₂CH₂—CH₂CH₃ H H H CH₂CH₂O—CH₂CH₂OH 195SO₂R₆R₇ H CH₂CH₂—CH₂CH₃ H H H CH₂—CH(OH)—CH₂OH 196 SO₂R₆R₇ HCH₂CH₂—CH₂CH₃ H H CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 197 SO₂R₆R₇ HCH₂CH₂—CH₂CH₃ H H CH₃ CH₂CH₂OH 198 SO₂R₆R₇ H CH₂CH₂—CH₂CH₃ H H CH₂CH₃CH₂CH₂OH 199 SO₂R₆R₇ H CH₂CH₂—CH₂CH₃ H H H CH(CH₃)—CH₂OH 200 SO₂R₆R₇ HCH₂CH₂—CH₂CH₃ H H H CH—(CH₂OH)—CH₂CH₃ 201 SO₂R₆R₇ H CH₂CH₂—CH₂CH₃ H H HCH₂CH₂SH 202 SO₂R₆R₇ H CH₂CH₂—CH₂CH₃ H H CH₂C₆H₅ CH₂CH₂OH 203 SO₂R₆R₇ HCH₂CH₂—CH₂CH₃ H H CH₂CH₂—CH₃ CH₂CH₂OH 204 SO₂R₆R₇ H CH₂CH₂—CH₂CH₃ H H HCH₂CH—(CH₃)OH 205 SO₂R₆R₇ H CH₂CH₂—CH₂CH₃ H H H CH₂CH₂—CH₂OH 206 SO₂R₆R₇H CH₂CH₂—CH₂CH₃ H H H CH₂CH₂—CH₂CH₂OH 207 SO₂R₆R₇ H CH₂CH₂—CH₂CH₃ H H HCH(CH₂—CH₂CH₃)—CH₂OH 208 SO₂R₆R₇ H CH₂CH₂—CH₂CH₃ H H CH(CH₃)₂ CH₂CH₂OH209 SO₂R₆R₇ H CH₂CH₂—CH₂CH₃ H H H CH—(CH₂OH)₂ 210 SO₂R₆R₇ HCH₂CH₂—CH₂CH₃ H H H CH₂—CH(OH)—CH₂CH₃ 211 CH(CH₃)₂ H SO₂R₆R₇ H H HCH₂CH₂OH 212 CH(CH₃)₂ H SO₂R₆R₇ H H CH₂CH₂OH CH₂CH₂OH 213 CH(CH₃)₂ HSO₂R₆R₇ H H H CH₂CH₂O—CH₂CH₂OH 214 CH(CH₃)₂ H SO₂R₆R₇ H H HCH₂—CH(OH)—CH₂OH 215 CH(CH₃)₂ H SO₂R₆R₇ H H CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH216 CH(CH₃)₂ H SO₂R₆R₇ H H CH₃ CH₂CH₂OH 217 CH(CH₃)₂ H SO₂R₆R₇ H HCH₂CH₃ CH₂CH₂OH 218 CH(CH₃)₂ H SO₂R₆R₇ H H H CH(CH₃)—CH₂OH 219 CH(CH₃)₂H SO₂R₆R₇ H H H CH—(CH₂OH)—CH₂CH₃ 220 CH(CH₃)₂ H SO₂R₆R₇ H H H CH₂CH₂SH221 CH(CH₃)₂ H SO₂R₆R₇ H H CH₂C₆H₅ CH₂CH₂OH 222 CH(CH₃)₂ H SO₂R₆R₇ H HCH₂CH₂—CH₃ CH₂CH₂OH 223 CH(CH₃)₂ H SO₂R₆R₇ H H H CH₂CH—(CH₃)OH 224CH(CH₃)₂ H SO₂R₆R₇ H H H CH₂CH₂—CH₂OH 225 CH(CH₃)₂ H SO₂R₆R₇ H H HCH₂CH₂—CH₂CH₂OH 226 CH(CH₃)₂ H SO₂R₆R₇ H H H CH(CH₂—CH₂CH₃)—CH₂OH 227CH(CH₃)₂ H SO₂R₆R₇ H H CH(CH₃)₂ CH₂CH₂OH 228 CH(CH₃)₂ H SO₂R₆R₇ H H HCH—(CH₂OH)₂ 229 CH(CH₃)₂ H SO₂R₆R₇ H H H CH₂—CH(OH)—CH₂CH₃ 230 SO₂R₆R₇ HC₆H₅ H H H CH₂CH₂OH 231 SO₂R₆R₇ H C₆H₅ H H CH₂CH₂OH CH₂CH₂OH 232 SO₂R₆R₇H C₆H₅ H H H CH₂CH₂O—CH₂CH₂OH 233 SO₂R₆R₇ H C₆H₅ H H H CH₂—CH(OH)—CH₂OH234 SO₂R₆R₇ H C₆H₅ H H CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 235 SO₂R₆R₇ H C₆H₅ HH CH₃ CH₂CH₂OH 236 SO₂R₆R₇ H C₆H₅ H H CH₂CH₃ CH₂CH₂OH 237 SO₂R₆R₇ H C₆H₅H H H CH(CH₃)—CH₂OH 238 SO₂R₆R₇ H C₆H₅ H H H CH—(CH₂OH)—CH₂CH₃ 239SO₂R₆R₇ H C₆H₅ H H H CH₂CH₂SH 240 SO₂R₆R₇ H C₆H₅ H H CH₂C₆H₅ CH₂CH₂OH241 SO₂R₆R₇ H C₆H₅ H H CH₂CH₂—CH₃ CH₂CH₂OH 242 SO₂R₆R₇ H C₆H₅ H H HCH₂CH—(CH₃)OH 243 SO₂R₆R₇ H C₆H₅ H H H CH₂CH₂—CH₂OH 244 SO₂R₆R₇ H C₆H₅ HH H CH₂CH₂—CH₂CH₂OH 245 SO₂R₆R₇ H C₆H₅ H H H CH(CH₂—CH₂CH₃)—CH₂OH 246SO₂R₆R₇ H C₆H₅ H H CH(CH₃)₂ CH₂CH₂OH 247 SO₂R₆R₇ H C₆H₅ H H HCH—(CH₂OH)₂ 248 SO₂R₆R₇ H C₆H₅ H H H CH₂—CH(OH)—CH₂CH₃ 249 SO₂R₆R₇ HOCH₂CH₃ H H H CH₂CH₂OH 250 SO₂R₆R₇ H OCH₂CH₃ H H CH₂CH₂OH CH₂CH₂OH 251SO₂R₆R₇ H OCH₂CH₃ H H H CH₂CH₂O—CH₂CH₂OH 252 SO₂R₆R₇ H OCH₂CH₃ H H HCH₂—CH(OH)—CH₂OH 253 SO₂R₆R₇ H OCH₂CH₃ H H CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH254 SO₂R₆R₇ H OCH₂CH₃ H H CH₃ CH₂CH₂OH 255 SO₂R₆R₇ H OCH₂CH₃ H H CH₂CH₃CH₂CH₂OH 256 SO₂R₆R₇ H OCH₂CH₃ H H H CH(CH₃)—CH₂OH 257 SO₂R₆R₇ H OCH₂CH₃H H H CH—(CH₂OH)—CH₂CH₃ 258 SO₂R₆R₇ H OCH₂CH₃ H H H CH₂CH₂SH 259 SO₂R₆R₇H OCH₂CH₃ H H CH₂C₆H₅ CH₂CH₂OH 260 SO₂R₆R₇ H OCH₂CH₃ H H CH₂CH₂—CH₃CH₂CH₂OH 261 SO₂R₆R₇ H OCH₂CH₃ H H H CH₂CH—(CH₃)OH 262 SO₂R₆R₇ H OCH₂CH₃H H H CH₂CH₂—CH₂OH 263 SO₂R₆R₇ H OCH₂CH₃ H H H CH₂CH₂—CH₂CH₂OH 264SO₂R₆R₇ H OCH₂CH₃ H H H CH(CH₂—CH₂CH₃)—CH₂OH 265 SO₂R₆R₇ H OCH₂CH₃ H HCH(CH₃)₂ CH₂CH₂OH 266 SO₂R₆R₇ H OCH₂CH₃ H H H CH—(CH₂OH)₂ 267 SO₂R₆R₇ HOCH₂CH₃ H H H CH₂—CH(OH)—CH₂CH₃ 268 SO₂R₆R₇ H SCH₂CH₃ H H H CH₂CH₂OH 269SO₂R₆R₇ H SCH₂CH₃ H H CH₂CH₂OH CH₂CH₂OH 270 SO₂R₆R₇ H SCH₂CH₃ H H HCH₂CH₂O—CH₂CH₂OH 271 SO₂R₆R₇ H SCH₂CH₃ H H H CH—CH(OH)—CH₂OH 272 SO₂R₆R₇H SCH₂CH₃ H H CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 273 SO₂R₆R₇ H SCH₂CH₃ H H CH₃CH₂CH₂OH 274 SO₂R₆R₇ H SCH₂CH₃ H H CH₂CH₃ CH₂CH₂OH 275 SO₂R₆R₇ H SCH₂CH₃H H H CH(CH₃)—CH₂OH 276 SO₂R₆R₇ H SCH₂CH₃ H H H CH—(CH₂OH)—CH₂CH₃ 277SO₂R₆R₇ H SCH₂CH₃ H H H CH₂CH₂SH 278 SO₂R₆R₇ H SCH₂CH₃ H H CH₂C₆H₅CH₂CH₂OH 279 SO₂R₆R₇ H SCH₂CH₃ H H CH₂CH₂—CH₃ CH₂CH₂OH 280 SO₂R₆R₇ HSCH₂CH₃ H H H CH₂CH—(CH₃)OH 281 SO₂R₆R₇ H SCH₂CH₃ H H H CH₂CH₂—CH₂OH 282SO₂R₆R₇ H SCH₂CH₃ H H H CH₂CH₂—CH₂CH₂OH 283 SO₂R₆R₇ H SCH₂CH₃ H H HCH(CH₂—CH₂CH₃)—CH₂OH 284 SO₂R₆R₇ H SCH₂CH₃ H H CH(CH₃)₂ CH₂CH₂OH 285SO₂R₆R₇ H SCH₂CH₃ H H H CH—(CH₂OH)₂ 286 SO₂R₆R₇ H SCH₂CH₃ H H HCH—CH(OH)—CH₂CH₃ 287 SO₂R₆R₇ H CH₃ H CH₃ H CH₂CH₂OH 288 SO₂R₆R₇ H CH₃ HCH₃ CH₂CH₂OH CH₂CH₂OH 289 SO₂R₆R₇ H CH₃ H CH₃ H CH₂CH₂O—CH₂CH₂OH 290SO₂R₆R₇ H CH₃ H CH₃ H CH₂—CH(OH)—CH₂OH 291 SO₂R₆R₇ H CH₃ H CH₃CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 292 SO₂R₆R₇ H CH₃ H CH₃ CH₃ CH₂CH₂OH 293SO₂R₆R₇ H CH₃ H CH₃ CH₂CH₃ CH₂CH₂OH 294 SO₂R₆R₇ H CH₃ H CH₃ HCH(CH₃)—CH₂OH 295 SO₂R₆R₇ H CH₃ H CH₃ H CH—(CH₂OH)—CH₂CH₃ 296 SO₂R₆R₇ HCH₃ H CH₃ H CH₂CH₂SH 297 SO₂R₆R₇ H CH₃ H CH₃ CH₂C₆H₅ CH₂CH₂OH 298SO₂R₆R₇ H CH₃ H CH₃ CH₂CH₂—CH₃ CH₂CH₂OH 299 SO₂R₆R₇ H CH₃ H CH₃ HCH₂CH—(CH₃)OH 300 SO₂R₆R₇ H CH₃ H CH₃ H CH₂CH₂—CH₂OH 301 SO₂R₆R₇ H CH₃ HCH₃ H CH₂CH₂—CH₂CH₂OH 302 SO₂R₆R₇ H CH₃ H CH₃ H CH(CH₂—CH₂CH₃)—CH₂OH 303SO₂R₆R₇ H CH₃ H CH₃ CH(CH₃)₂ CH₂CH₂OH 304 SO₂R₆R₇ H CH₃ H CH₃ HCH—(CH₂OH)₂ 305 SO₂R₆R₇ H CH₃ H CH₃ H CH₂—CH(OH)—CH₂CH₃ 306 H CH₃SO₂R₆R₇ H CH₃ H CH₂CH₂OH 307 H CH₃ SO₂R₆R₇ H CH₃ CH₂CH₂OH CH₂CH₂OH 308 HCH₃ SO₂R₆R₇ H CH₃ H CH₂CH₂O—CH₂CH₂OH 309 H CH₃ SO₂R₆R₇ H CH₃ HCH₂—CH(OH)—CH₂OH 310 H CH₃ SO₂R₆R₇ H CH₃ CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 311H CH₃ SO₂R₆R₇ H CH₃ CH₃ CH₂CH₂OH 312 H CH₃ SO₂R₆R₇ H CH₃ CH₂CH₃ CH₂CH₂OH313 H CH₃ SO₂R₆R₇ H CH₃ H CH(CH₃)—CH₂OH 314 H CH₃ SO₂R₆R₇ H CH₃ HCH—(CH₂OH)—CH₂CH₃ 315 H CH₃ SO₂R₆R₇ H CH₃ H CH₂CH₂SH 316 H CH₃ SO₂R₆R₇ HCH₃ CH₂C₆H₅ CH₂CH₂OH 317 H CH₃ SO₂R₆R₇ H CH₃ CH₂CH₂—CH₃ CH₂CH₂OH 318 HCH₃ SO₂R₆R₇ H CH₃ H CH₂CH—(CH₃)OH 319 H CH₃ SO₂R₆R₇ H CH₃ H CH₂CH₂—CH₂OH320 H CH₃ SO₂R₆R₇ H CH₃ H CH₂CH₂—CH₂CH₂OH 321 H CH₃ SO₂R₆R₇ H CH₃ HCH(CH₂—CH₂CH₃)—CH₂OH 322 H CH₃ SO₂R₆R₇ H CH₃ CH(CH₃)₂ CH₂CH₂OH 323 H CH₃SO₂R₆R₇ H CH₃ H CH—(CH₂OH)₂ 324 H CH₃ SO₂R₆R₇ H CH₃ H CH—CH(OH)—CH₂CH₃325 CH₃ H SO₂R₆R₇ H CH₃ H CH₂CH₂OH 326 CH₃ H SO₂R₆R₇ H CH₃ CH₂CH₂OHCH₂CH₂OH 327 CH₃ H SO₂R₆R₇ H CH₃ H CH₂CH₂O—CH₂CH₂OH 328 CH₃ H SO₂R₆R₇ HCH₃ H CH₂—CH(OH)—CH₂OH 329 CH₃ H SO₂R₆R₇ H CH₃ CH₂CH—(CH₃)OHCH₂CH—(CH₃)OH 330 CH₃ H SO₂R₆R₇ H CH₃ CH₃ CH₂CH₂OH 331 CH₃ H SO₂R₆R₇ HCH₃ CH₂CH₃ CH₂CH₂OH 332 CH₃ H SO₂R₆R₇ H CH₃ H CH(CH₃)—CH₂OH 333 CH₃ HSO₂R₆R₇ H CH₃ H CH—(CH₂OH)—CH₂CH₃ 334 CH₃ H SO₂R₆R₇ H CH₃ H CH₂CH₂SH 335CH₃ H SO₂R₆R₇ H CH₃ CH₂C₆H₅ CH₂CH₂OH 336 CH₃ H SO₂R₆R₇ H CH₃ CH₂CH₂—CH₃CH₂CH₂OH 337 CH₃ H SO₂R₆R₇ H CH₃ H CH₂CH—(CH₃)OH 338 CH₃ H SO₂R₆R₇ H CH₃H CH₂CH₂—CH₂OH 339 CH₃ H SO₂R₆R₇ H CH₃ H CH₂CH₂—CH₂CH₂OH 340 CH₃ HSO₂R₆R₇ H CH₃ H CH(CH₂—CH₂CH₃)—CH₂OH 341 CH₃ H SO₂R₆R₇ H CH₃ CH(CH₃)₂CH₂CH₂OH 342 CH₃ H SO₂R₆R₇ H CH₃ H CH—(CH₂OH)₂ 343 CH₃ H SO₂R₆R₇ H CH₃ HCH₂—CH(OH)—CH₂CH₃ 344 SO₂R₆R₇ H OCH₃ H CH₃ H CH₂CH₂OH 345 SO₂R₆R₇ H OCH₃H CH₃ CH₂CH₂OH CH₂CH₂OH 346 SO₂R₆R₇ H OCH₃ H CH₃ H CH₂CH₂O—CH₂CH₂OH 347SO₂R₆R₇ H OCH₃ H CH₃ H CH₂—CH(OH)—CH₂OH 348 SO₂R₆R₇ H OCH₃ H CH₃CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 349 SO₂R₆R₇ H OCH₃ H CH₃ CH₃ CH₂CH₂OH 350SO₂R₆R₇ H OCH₃ H CH₃ CH₂CH₃ CH₂CH₂OH 351 SO₂R₆R₇ H OCH₃ H CH₃ HCH(CH₃)—CH₂OH 352 SO₂R₆R₇ H OCH₃ H CH₃ H CH—(CH₂OH)—CH₂CH₃ 353 SO₂R₆R₇ HOCH₃ H CH₃ H CH₂CH₂SH 354 SO₂R₆R₇ H OCH₃ H CH₃ CH₂C₆H₅ CH₂CH₂OH 355SO₂R₆R₇ H OCH₃ H CH₃ CH₂CH₂—CH₃ CH₂CH₂OH 356 SO₂R₆R₇ H OCH₃ H CH₃ HCH₂CH—(CH₃)OH 357 SO₂R₆R₇ H OCH₃ H CH₃ H CH₂CH₂—CH₂OH 358 SO₂R₆R₇ H OCH₃H CH₃ H CH₂CH₂—CH₂CH₂OH 359 SO₂R₆R₇ H OCH₃ H CH₃ H CH(CH₂—CH₂CH₃)—CH₂OH360 SO₂R₆R₇ H OCH₃ H CH₃ CH(CH₃)₂ CH₂CH₂OH 361 SO₂R₆R₇ H OCH₃ H CH₃ HCH—(CH₂OH)₂ 362 SO₂R₆R₇ H OCH₃ H CH₃ H CH₂—CH(OH)—CH₂CH₃ 363 SO₂R₆R₇ HCH₃ CH₃ H H CH₂CH₂OH 364 SO₂R₆R₇ H CH₃ CH₃ H CH₂CH₂OH CH₂CH₂OH 365SO₂R₆R₇ H CH₃ CH₃ H H CH₂CH₂O—CH₂CH₂OH 366 SO₂R₆R₇ H CH₃ CH₃ H HCH₂—CH(OH)—CH₂OH 367 SO₂R₆R₇ H CH₃ CH₃ H CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 368SO₂R₆R₇ H CH₃ CH₃ H CH₃ CH₂CH₂OH 369 SO₂R₆R₇ H CH₃ CH₃ H CH₂CH₃ CH₂CH₂OH370 SO₂R₆R₇ H CH₃ CH₃ H H CH(CH₃)—CH₂OH 371 SO₂R₆R₇ H CH₃ CH₃ H HCH—(CH₂OH)—CH₂CH₃ 372 SO₂R₆R₇ H CH₃ CH₃ H H CH₂CH₂SH 373 SO₂R₆R₇ H CH₃CH₃ H CH₂C₆H₅ CH₂CH₂OH 374 SO₂R₆R₇ H CH₃ CH₃ H CH₂CH₂—CH₃ CH₂CH₂OH 375SO₂R₆R₇ H CH₃ CH₃ H H CH₂CH—(CH₃)OH 376 SO₂R₆R₇ H CH₃ CH₃ H HCH₂CH₂—CH₂OH 377 SO₂R₆R₇ H CH₃ CH₃ H H CH₂CH₂—CH₂CH₂OH 378 SO₂R₆R₇ H CH₃CH₃ H H CH(CH₂—CH₂CH₃)—CH₂OH 379 SO₂R₆R₇ H CH₃ CH₃ H CH(CH₃)₂ CH₂CH₂OH380 SO₂R₆R₇ H CH₃ CH₃ H H CH—(CH₂OH)₂ 381 SO₂R₆R₇ H CH₃ CH₃ H HCH₂—CH(OH)—CH₂CH₃ 382 CH₃ SO₂R₆R₇ CH₃ H CH₃ H CH₂CH₂OH 383 CH₃ SO₂R₆R₇CH₃ H CH₃ CH₂CH₂OH CH₂CH₂OH 384 CH₃ SO₂R₆R₇ CH₃ H CH₃ H CH₂CH₂O—CH₂CH₂OH385 CH₃ SO₂R₆R₇ CH₃ H CH₃ H CH₂—CH(OH)—CH₂OH 386 CH₃ SO₂R₆R₇ CH₃ H CH₃CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 387 CH₃ SO₂R₆R₇ CH₃ H CH₃ CH₃ CH₂CH₂OH 388CH₃ SO₂R₆R₇ CH₃ H CH₃ CH₂CH₃ CH₂CH₂OH 389 CH₃ SO₂R₆R₇ CH₃ H CH₃ HCH(CH₃)—CH₂OH 390 CH₃ SO₂R₆R₇ CH₃ H CH₃ H CH—(CH₂OH)—CH₂CH₃ 391 CH₃SO₂R₆R₇ CH₃ H CH₃ H CH₂CH₂SH 392 CH₃ SO₂R₆R₇ CH₃ H CH₃ CH₂C₆H₅ CH₂CH₂OH393 CH₃ SO₂R₆R₇ CH₃ H CH₃ CH₂CH₂—CH₃ CH₂CH₂OH 394 CH₃ SO₂R₆R₇ CH₃ H CH₃H CH₂CH—(CH₃)OH 395 CH₃ SO₂R₆R₇ CH₃ H CH₃ H CH₂CH₂—CH₂OH 396 CH₃ SO₂R₆R₇CH₃ H CH₃ H CH₂CH₂—CH₂CH₂OH 397 CH₃ SO₂R₆R₇ CH₃ H CH₃ HCH(CH₂—CH₂CH₃)—CH₂OH 398 CH₃ SO₂R₆R₇ CH₃ H CH₃ CH(CH₃)₂ CH₂CH₂OH 399 CH₃SO₂R₆R₇ CH₃ H CH₃ H CH—(CH₂OH)₂ 400 CH₃ SO₂R₆R₇ CH₃ H CH₃ HCH₂—CH(OH)—CH₂CH₃ 401 CH₃ SO₂R₆R₇ CH₃ CH₃ H H CH₂CH₂OH 402 CH₃ SO₂R₆R₇CH₃ CH₃ H CH₂CH₂OH CH₂CH₂OH 403 CH₃ SO₂R₆R₇ CH₃ CH₃ H H CH₂CH₂O—CH₂CH₂OH404 CH₃ SO₂R₆R₇ CH₃ CH₃ H H CH₂—CH(OH)—CH₂OH 405 CH₃ SO₂R₆R₇ CH₃ CH₃ HCH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 406 CH₃ SO₂R₆R₇ CH₃ CH₃ H CH₃ CH₂CH₂OH 407CH₃ SO₂R₆R₇ CH₃ CH₃ H CH₂CH₃ CH₂CH₂OH 408 CH₃ SO₂R₆R₇ CH₃ CH₃ H HCH(CH₃)—CH₂OH 409 CH₃ SO₂R₆R₇ CH₃ CH₃ H H CH—(CH₂OH)—CH₂CH₃ 410 CH₃SO₂R₆R₇ CH₃ CH₃ H H CH₂CH₂SH 411 CH₃ SO₂R₆R₇ CH₃ CH₃ H CH₂C₆H₅ CH₂CH₂OH412 CH₃ SO₂R₆R₇ CH₃ CH₃ H CH₂CH₂—CH₃ CH₂CH₂OH 413 CH₃ SO₂R₆R₇ CH₃ CH₃ HH CH₂CH₂—(CH₃)OH 414 CH₃ SO₂R₆R₇ CH₃ CH₃ H H CH₂CH₂—CH₂OH 415 CH₃SO₂R₆R₇ CH₃ CH₃ H H CH₂CH₂—CH₂CH₂OH 416 CH₃ SO₂R₆R₇ CH₃ CH₃ H HCH(CH₂—CH₂CH₃)—CH₂OH 417 CH₃ SO₂R₆R₇ CH₃ CH₃ H CH(CH₃)₂ CH₂CH₂OH 418 CH₃SO₂R₆R₇ CH₃ CH₃ H H CH—(CH₂OH)₂ 419 CH₃ SO₂R₆R₇ CH₃ CH₃ H HCH₂—CH(OH)—CH₂CH₃ 420 H CH₃ SO₂R₆R₇ H OCH₃ H CH₂CH₂OH 421 H CH₃ SO₂R₆R₇H OCH₃ CH₂CH₂OH CH₂CH₂OH 422 H CH₃ SO₂R₆R₇ H OCH₃ H CH₂CH₂O—CH₂CH₂OH 423H CH₃ SO₂R₆R₇ H OCH₃ H CH₂—CH(OH)—CH₂OH 424 H CH₃ SO₂R₆R₇ H OCH₃CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 425 H CH₃ SO₂R₆R₇ H OCH₃ CH₃ CH₂CH₂OH 426 HCH₃ SO₂R₆R₇ H OCH₃ CH₂CH₃ CH₂CH₂OH 427 H CH₃ SO₂R₆R₇ H OCH₃ HCH(CH₃)—CH₂OH 428 H CH₃ SO₂R₆R₇ H OCH₃ H CH—(CH₂OH)—CH₂CH₃ 429 H CH₃SO₂R₆R₇ H OCH₃ H CH₂CH₂SH 430 H CH₃ SO₂R₆R₇ H OCH₃ CH₂C₆H₅ CH₂CH₂OH 431H CH₃ SO₂R₆R₇ H OCH₃ CH₂CH₂—CH₃ CH₂CH₂OH 432 H CH₃ SO₂R₆R₇ H OCH₃ HCH₂CH—(CH₃)OH 433 H CH₃ SO₂R₆R₇ H OCH₃ H CH₂CH₂—CH₂OH 434 H CH₃ SO₂R₆R₇H OCH₃ H CH₂CH₂—CH₂CH₂OH 435 H CH₃ SO₂R₆R₇ H OCH₃ H CH(CH₂—CH₂CH₃)—CH₂OH436 H CH₃ SO₂R₆R₇ H OCH₃ CH(CH₃)₂ CH₂CH₂OH 437 H CH₃ SO₂R₆R₇ H OCH₃ HCH—(CH₂OH)₂ 438 H CH₃ SO₂R₆R₇ H OCH₃ H CH₂—CH(OH)—CH₂CH₃ 439 H CH₃SO₂R₆R₇ H CH₃ H CH₂CH₂OH 440 H CH₃ SO₂R₆R₇ H CH₃ CH₂CH₂OH CH₂CH₂OH 441 HCH₃ SO₂R₆R₇ H CH₃ H CH₂CH₂O—CH₂CH₂OH 442 H CH₃ SO₂R₆R₇ H CH₃ HCH₂—CH(OH)—CH₂OH 443 H CH₃ SO₂R₆R₇ H CH₃ CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 444H CH₃ SO₂R₆R₇ H CH₃ CH₃ CH₂CH₂OH 445 H CH₃ SO₂R₆R₇ H CH₃ CH₂CH₃ CH₂CH₂OH446 H CH₃ SO₂R₆R₇ H CH₃ H CH(CH₃)—CH₂OH 447 H CH₃ SO₂R₆R₇ H CH₃ HCH—(CH₂OH)—CH₂CH₃ 448 H CH₃ SO₂R₆R₇ H CH₃ H CH₂CH₂SH 449 H CH₃ SO₂R₆R₇ HCH₃ CH₂C₆H₅ CH₂CH₂OH 450 H CH₃ SO₂R₆R₇ H CH₃ CH₂CH₂—CH₃ CH₂CH₂OH 451 HCH₃ SO₂R₆R₇ H CH₃ H CH₂CH—(CH₃)OH 452 H CH₃ SO₂R₆R₇ H CH₃ H CH₂CH₂—CH₂OH453 H CH₃ SO₂R₆R₇ H CH₃ H CH₂CH₂—CH₂CH₂OH 454 H CH₃ SO₂R₆R₇ H CH₃ HCH(CH₂—CH₂CH₃)—CH₂OH 455 H CH₃ SO₂R₆R₇ H CH₃ CH(CH₃)₂ CH₂CH₂OH 456 H CH₃SO₂R₆R₇ H CH₃ H CH—(CH₂OH)₂ 457 H CH₃ SO₂R₆R₇ H CH₃ H CH₂—CH(OH)—CH₂CH₃458 CH₃ H SO₂R₆R₇ H t-C₄H₉ H CH₂CH₂OH 459 CH₃ H SO₂R₆R₇ H t-C₄H₉CH₂CH₂OH CH₂CH₂OH 460 CH₃ H SO₂R₆R₇ H t-C₄H₉ H CH₂CH₂O—CH₂CH₂OH 461 CH₃H SO₂R₆R₇ H t-C₄H₉ H CH₂—CH(OH)—CH₂OH 462 CH₃ H SO₂R₆R₇ H t-C₄H₉CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 463 CH₃ H SO₂R₆R₇ H t-C₄H₉ CH₃ CH₂CH₂OH 464CH₃ H SO₂R₆R₇ H t-C₄H₉ CH₂CH₃ CH₂CH₂OH 465 CH₃ H SO₂R₆R₇ H t-C₄H₉ HCH(CH₃)—CH₂OH 466 CH₃ H SO₂R₆R₇ H t-C₄H₉ H CH—(CH₂OH)—CH₂CH₃ 467 CH₃ HSO₂R₆R₇ H t-C₄H₉ H CH₂CH₂SH 468 CH₃ H SO₂R₆R₇ H t-C₄H₉ CH₂C₆H₅ CH₂CH₂OH469 CH₃ H SO₂R₆R₇ H t-C₄H₉ CH₂CH₂—CH₃ CH₂CH₂OH 470 CH₃ H SO₂R₆R₇ Ht-C₄H₉ H CH₂CH—(CH₃)OH 471 CH₃ H SO₂R₆R₇ H t-C₄H₉ H CH₂CH₂—CH₂OH 472 CH₃H SO₂R₆R₇ H t-C₄H₉ H CH₂CH₂—CH₂CH₂OH 473 CH₃ H SO₂R₆R₇ H t-C₄H₉ HCH(CH₂—CH₂CH₃)—CH₂OH 474 CH₃ H SO₂R₆R₇ H t-C₄H₉ CH(CH₃)₂ CH₂CH₂OH 475CH₃ H SO₂R₆R₇ H t-C₄H₉ H CH—(CH₂OH)₂ 476 CH₃ H SO₂R₆R₇ H t-C₄H₉ HCH₂—CH(OH)—CH₂CH₃ 477 SO₂R₆R₇ H OCH₃ H OCH₃ H CH₂CH₂OH 478 SO₂R₆R₇ HOCH₃ H OCH₃ CH₂CH₂OH CH₂CH₂OH 479 SO₂R₆R₇ H OCH₃ H OCH₃ HCH₂CH₂O—CH₂CH₂OH 480 SO₂R₆R₇ H OCH₃ H OCH₃ H CH₂—CH(OH)—CH₂OH 481SO₂R₆R₇ H OCH₃ H OCH₃ CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 482 SO₂R₆R₇ H OCH₃ HOCH₃ CH₃ CH₂CH₂OH 483 SO₂R₆R₇ H OCH₃ H OCH₃ CH₂CH₃ CH₂CH₂OH 484 SO₂R₆R₇H OCH₃ H OCH₃ H CH(CH₃)—CH₂OH 485 SO₂R₆R₇ H OCH₃ H OCH₃ HCH—(CH₂OH)—CH₂CH₃ 486 SO₂R₆R₇ H OCH₃ H OCH₃ H CH₂CH₂SH 487 SO₂R₆R₇ HOCH₃ H OCH₃ CH₂C₆H₅ CH₂CH₂OH 488 SO₂R₆R₇ H OCH₃ H OCH₃ CH₂CH₂—CH₃CH₂CH₂OH 489 SO₂R₆R₇ H OCH₃ H OCH₃ H CH₂CH—(CH₃)OH 490 SO₂R₆R₇ H OCH₃ HOCH₃ H CH₂CH₂—CH₂OH 491 SO₂R₆R₇ H OCH₃ H OCH₃ H CH₂CH₂—CH₂CH₂OH 492SO₂R₆R₇ H OCH₃ H OCH₃ H CH(CH₂—CH₂CH₃)—CH₂OH 493 SO₂R₆R₇ H OCH₃ H OCH₃CH(CH₃)₂ CH₂CH₂OH 494 SO₂R₆R₇ H OCH₃ H OCH₃ H CH—(CH₂OH)₂ 495 SO₂R₆R₇ HOCH₃ H OCH₃ H CH₂—CH(OH)—CH₂CH₃ 496 SO₂R₆R₇ CH₃ OCH₃ CH₃ H H CH₂CH₂OH497 SO₂R₆R₇ CH₃ OCH₃ CH₃ H CH₂CH₂OH CH₂CH₂OH 498 SO₂R₆R₇ CH₃ OCH₃ CH₃ HH CH₂CH₂O—CH₂CH₂OH 499 SO₂R₆R₇ CH₃ OCH₃ CH₃ H H CH₂—CH(OH)—CH₂OH 500SO₂R₆R₇ CH₃ OCH₃ CH₃ H CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 501 SO₂R₆R₇ CH₃ OCH₃CH₃ H CH₃ CH₂CH₂OH 502 SO₂R₆R₇ CH₃ OCH₃ CH₃ H CH₂CH₃ CH₂CH₂OH 503SO₂R₆R₇ CH₃ OCH₃ CH₃ H H CH(CH₃)—CH₂OH 504 SO₂R₆R₇ CH₃ OCH₃ CH₃ H HCH—(CH₂OH)—CH₂CH₃ 505 SO₂R₆R₇ CH₃ OCH₃ CH₃ H H CH₂CH₂SH 506 SO₂R₆R₇ CH₃OCH₃ CH₃ H CH₂C₆H₅ CH₂CH₂OH 507 SO₂R₆R₇ CH₃ OCH₃ CH₃ H CH₂CH₂—CH₃CH₂CH₂OH 508 SO₂R₆R₇ CH₃ OCH₃ CH₃ H H CH₂CH—(CH₃)OH 509 SO₂R₆R₇ CH₃ OCH₃CH₃ H H CH₂CH₂—CH₂OH 510 SO₂R₆R₇ CH₃ OCH₃ CH₃ H H CH₂CH₂—CH₂CH₂OH 511SO₂R₆R₇ CH₃ OCH₃ CH₃ H H CH(CH₂—CH₂CH₃)—CH₂OH 512 SO₂R₆R₇ CH₃ OCH₃ CH₃ HCH(CH₃)₂ CH₂CH₂OH 513 SO₂R₆R₇ CH₃ OCH₃ CH₃ H H CH—(CH₂OH)₂ 514 SO₂R₆R₇CH₃ OCH₃ CH₃ H H CH₂—CH(OH)—CH₂CH₃ 515 SO₂R₆R₇ H

H H H CH₂CH₂OH 516 SO₂R₆R₇ H

H H CH₂CH₂OH CH₂CH₂OH 517 SO₂R₆R₇ H

H H H CH₂CH₂O—CH₂CH₂OH 518 SO₂R₆R₇ H

H H H CH₂—CH(OH)—CH₂OH 519 SO₂R₆R₇ H

H H CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 520 SO₂R₆R₇ H

H H CH₃ CH₂CH₂OH 521 SO₂R₆R₇ H

H H CH₂CH₃ CH₂CH₂OH 522 SO₂R₆R₇ H

H H H CH(CH₃)—CH₂OH 523 SO₂R₆R₇ H

H H H CH—(CH₂OH)—CH₂CH₃ 524 SO₂R₆R₇ H

H H H CH₂CH₂SH 525 SO₂R₆R₇ H

H H CH₂C₆H₅ CH₂CH₂OH 526 SO₂R₆R₇ H

H H CH₂CH₂—CH₃ CH₂CH₂OH 527 SO₂R₆R₇ H

H H H CH₂CH—(CH₃)OH 528 SO₂R₆R₇ H

H H H CH₂CH₂—CH₂OH 529 SO₂R₆R₇ H

H H H CH₂CH₂—CH₂CH₂OH 530 SO₂R₆R₇ H

H H H CH(CH₂—CH₂CH₃)—CH₂OH 531 SO₂R₆R₇ H

H H CH(CH₃)₂ CH₂CH₂OH 532 SO₂R₆R₇ H

H H H CH—(CH₂OH)₂ 533 SO₂R₆R₇ H

H H H CH₂—CH(OH)—CH₂CH₃ 534 SO₂R₆R₇ H

H H H CH₂CH₂OH 535 SO₂R₆R₇ H

H H CH₂CH₂OH CH₂CH₂OH 536 SO₂R₆R₇ H

H H H CH₂CH₂O—CH₂CH₂OH 537 SO₂R₆R₇ H

H H H CH₂—CH(OH)—CH₂OH 538 SO₂R₆R₇ H

H H CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 539 SO₂R₆R₇ H

H H CH₃ CH₂CH₂OH 540 SO₂R₆R₇ H

H H CH₂CH₃ CH₂CH₂OH 541 SO₂R₆R₇ H

H H H CH(CH₃)—CH₂OH 542 SO₂R₆R₇ H

H H H CH—(CH₂OH)—CH₂CH₃ 543 SO₂R₆R₇ H

H H H CH₂CH₂SH 544 SO₂R₆R₇ H

H H CH₂C₆H₅ CH₂CH₂OH 545 SO₂R₆R₇ H

H H CH₂CH₂—CH₃ CH₂CH₂OH 546 SO₂R₆R₇ H

H H H CH₂CH—(CH₃)OH 547 SO₂R₆R₇ H

H H H CH₂CH₂—CH₂OH 548 SO₂R₆R₇ H

H H H CH₂CH₂—CH₂CH₂OH 549 SO₂R₆R₇ H

H H H CH(CH₂—CH₂CH₃)—CH₂OH 550 SO₂R₆R₇ H

H H CH(CH₃)₂ CH₂CH₂OH 551 SO₂R₆R₇ H

H H H CH—(CH₂OH)₂ 552 SO₂R₆R₇ H

H H H CH₂—CH(OH)—CH₂CH₃ 553 CH₃ CH₃ SO₂R₆R₇ CH₃ CH₃ H CH₂CH₂OH 554 CH₃CH₃ SO₂R₆R₇ CH₃ CH₃ CH₂CH₂OH CH₂CH₂OH 555 CH₃ CH₃ SO₂R₆R₇ CH₃ CH₃ HCH₂CH₂O—CH₂CH₂OH 556 CH₃ CH₃ SO₂R₆R₇ CH₃ CH₃ H CH₂—CH(OH)—CH₂OH 557 CH₃CH₃ SO₂R₆R₇ CH₃ CH₃ CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 558 CH₃ CH₃ SO₂R₆R₇ CH₃CH₃ CH₃ CH₂CH₂OH 559 CH₃ CH₃ SO₂R₆R₇ CH₃ CH₃ CH₂CH₃ CH₂CH₂OH 560 CH₃ CH₃SO₂R₆R₇ CH₃ CH₃ H CH(CH₃)—CH₂OH 561 CH₃ CH₃ SO₂R₆R₇ CH₃ CH₃ HCH—(CH₂OH)—CH₂CH₃ 562 CH₃ CH₃ SO₂R₆R₇ CH₃ CH₃ H CH₂CH₂SH 563 CH₃ CH₃SO₂R₆R₇ CH₃ CH₃ CH₂C₆H₅ CH₂CH₂OH 564 CH₃ CH₃ SO₂R₆R₇ CH₃ CH₃ CH₂CH₂—CH₃CH₂CH₂OH 565 CH₃ CH₃ SO₂R₆R₇ CH₃ CH₃ H CH₂CH—(CH₃)OH 566 CH₃ CH₃ SO₂R₆R₇CH₃ CH₃ H CH₂CH₂—CH₂OH 567 CH₃ CH₃ SO₂R₆R₇ CH₃ CH₃ H CH₂CH₂—CH₂CH₂OH 568CH₃ CH₃ SO₂R₆R₇ CH₃ CH₃ H CH(CH₂—CH₂CH₃)—CH₂OH 569 CH₃ CH₃ SO₂R₆R₇ CH₃CH₃ CH(CH₃)₂ CH₂CH₂OH 570 CH₃ CH₃ SO₂R₆R₇ CH₃ CH₃ H CH—(CH₂OH)₂ 571 CH₃CH₃ SO₂R₆R₇ CH₃ CH₃ H CH₂—CH(OH)—CH₂CH₃ 572 SO₂R₆R₇ H

H H H CH₂CH₂OH 573 SO₂R₆R₇ H

H H CH₂CH₂OH CH₂CH₂OH 574 SO₂R₆R₇ H

H H H CH₂CH₂O—CH₂CH₂OH 575 SO₂R₆R₇ H

H H H CH₂—CH(OH)—CH₂OH 576 SO₂R₆R₇ H

H H CH₂CH—(CH₃)OH CH₂CH—(CH₃)OH 577 SO₂R₆R₇ H

H H CH₃ CH₂CH₂OH 578 SO₂R₆R₇ H

H H CH₂CH₃ CH₂CH₂OH 579 SO₂R₆R₇ H

H H H CH(CH₃)—CH₂OH 580 SO₂R₆R₇ H

H H H CH—(CH₂OH)—CH₂CH₃ 581 SO₂R₆R₇ H

H H H CH₂CH₂SH 582 SO₂R₆R₇ H

H H CH₂C₆H₅ CH₂CH₂OH 583 SO₂R₆R₇ H

H H CH₂CH₂—CH₃ CH₂CH₂OH 584 SO₂R₆R₇ H

H H H CH₂CH—(CH₃)OH 585 SO₂R₆R₇ H

H H H CH₂CH₂—CH₂OH 586 SO₂R₆R₇ H

H H H CH₂CH₂—CH₂CH₂OH 587 SO₂R₆R₇ H

H H H CH(CH₂—CH₂CH₃)—CH₂OH 588 SO₂R₆R₇ H

H H CH(CH₃)₂ CH₂CH₂OH 589 SO₂R₆R₇ H

H H H CH—(CH₂OH)₂

EXAMPLES 590-594 General Procedure

A formulation containing a colourant, an acrylic acid/acrylate polymericresin binder, an organic solvent, a photoinitiator, a polymerisablemonomer and optionally a dispersant is homogenized by stirring andfiltered over a 0.45 μm Teflon® filter. Spin coating of this formulationis performed on 52 mm×76 mm glass plates at various spinning speeds inorder to achieve various layer thicknesses. Soft bake at 80-100° C. for2 minutes affords the required thin transparent layer. UV exposurethrough a mask for 30 seconds followed by basic aqueous development andfinal post bake for 5 minutes at 200° C. results in a structuredpattern. Patterning is realised by irradiation through a mask enablingresolution ranging from 100 μm to 1 μm. The irradiation bandwidth of theUV lamp ranges from 300 nm to 410 nm with an energy intensity of 1.4mW/cm². The developing bath is an aqueous basic developer prepared fromcommercial JSR 4625™ in 2% concentration.

EXAMPLES 590-594

The compounds of examples 2, 3, 4, 5 and 6 are tested according to abovegeneral procedure, using following liquid formulation (liq):

-   -   1.92 parts Disperbyk® 161 (cationic polyurethane, dispersing        agent)    -   9 parts acrylic acid/acrylate resin binder    -   12.5 parts N-methylpyrrolidone (NMP)    -   2.3 parts Sartomer® 399 (dipentaerytritol pentaacrylate)    -   0.08 parts        2,4-bis(trichloromethyl)-6-(4-methoxyphenyl)-1,3,5-triazine

The results in the below table correspond to the baked layer (5 minutes@ 200° C.). The contrast is measured on a TSUBOSAKA ELECTRIC apparatus.

thick- colourant (liq) speed ness example ex. [g] [g] [rpm] x y Ycontrast [μm] 590 2 0.55 5.10 1000 0.397 0.460 93.88 4001 2.58 500 0.4250.495 91.04 3990 4.84 591 3 0.41 4.11 1000 0.415 0.473 98.79 2.78 5000.432 0.498 95.64 4.42 592 4 0.41 4.12 1000 0.412 0.469 97.57 2.67 5000.429 0.495 95.97 5.20 593 5 0.41 4.11 1000 0.426 0.487 96.64 2.68 5000.433 0.498 94.21 5.62 594 6 0.41 4.11 1000 0.399 0.450 99.36 2.67 5000.429 0.495 96.21 0.485

EXAMPLES 595-599

It is proceeded as in examples 590-594, with the difference that asimilar layer comprising C. I. Pigment Green 36 is first coated on theglass plate, on top of which the layers comprising the compounds ofexamples 2, 3, 4, 5 and 6 are coated after baking of the first greenlayer.

EXAMPLE 600

It is proceeded as in examples 595-599, with the difference that a layercomprising the compounds of example 1 is coated onto the layercomprising C. I. Pigment Green 36.

EXAMPLES 601-606

It is proceeded as in examples 595-600, with the difference that C. I.Pigment Green 7 is used instead of C. I. Pigment Green 36.

1. A colourant composition comprising in a weight ratio of from 99:1 to10:90, a pigment of average particle size from 10 to 200 nm and acompound of the formula

wherein R₁, R₂, R₃, R₄, R₅, R₆, R₇, R₈ and R₉ are, each independently ofall others, H, Br, Cl, F, SOR₁₀, SO₂R₁₀, SO₃R₁₀, SO₂NR₁₁R₁₂, NO₂, CN,COR₁₀, COOR₁₀ or CONR₁₁R₁₂; C₁-C₁₂alkyl, C₃-C₁₂cycloalkyl,C₂-C₁₂alkenyl, C₃-C₁₂cycloalkenyl or C₂-C₁₂alkynyl, each of which isunsubstituted or substituted one or several times by Cl, F, OH, OR₁₀,SR₁₀, SOR₁₀, SO₂R₁₀, NR₁₁R₁₂, CN, COR₁₀, COOR₁₀ or CONR₁₁R₁₂;C₇-C₁₂aralkyl or C₆-C₁₂aryl, each of which is unsubstituted orsubstituted one or several times by SO₃R₁₀, SO₂NR₁₁R₁₂, NO₂, Br, Cl, F,OH, OR₁₀, SR₁₀, SOR₁₀, SO₂R₁₀, NR₁₁R₁₂, CN, COR₁₀, COOR₁₀ or CONR₁₁R₁₂;or any of R₁, R₂, R₃, R₄ and R₅ is, each independently of all others,OH, OR₁₀, SR₁₀, SOR₁₀, SO₂R₁₀, or NR₁₁R₁₂; or R₄ is together with R₃ orwith R₅ 1,3-propylen, 1,3-propenylen, 1,4-butylen, 1,4-buten(1)ylen or1,4-buten(2)ylen, each of which is unsubstituted or substituted one orseveral times by Cl, F, OH, OR₁₀, SR₁₀, SOR₁₀, SO₂R₁₀, NR₁₁R₁₂, CN,COR₁₀, COOR₁₀ or CONR₁₁R₁₂, or 1,4-butadienylen which is unsubstitutedor substituted one or several times by SO₃R₁₀, SO₂NR₁₁R₁₂, NO₂, Br, Cl,F, OH, OR₁₀, SR₁₀, SOR₁₀, SO₂R₁₀, NR₁₁R₁₂, CN, COR₁₀, COOR₁₀ orCONR₁₁R₁₂; or R₆ is a radical of formula

or R₇ is a direct bond from C in position 1 or 2 of the anthraquinonesubstructure to R₁; R₁₀ is [C₂-C₆alkylene-O]_(n)C₁-C₁₂alkyl,[C₂-C₆alkylene-NH]_(n)C₁-C₁₂alkyl, C₁-C₁₂alkyl, C₃-C₁₂cycloalkyl,C₂-C₁₂alkenyl, C₃-C₁₂cycloalkenyl or C₂-C₁₂alkynyl, each of which isunsubstituted or substituted one or several times by Cl, F, OR₂₁,NR₂₂R₂₃, CN, COR₂₁, COOR₂₁ or CONR₂₂R₂₃; C₇-C₁₂aralkyl or C₆-C₁₂aryl,each of which is unsubstituted or substituted one or several times byNO₂, SOR₂₁, SO₂R₂₁, SO₃R₂₁, SO₂NR₂₂R₂₃, Br, Cl, F, OR₂₁, SR₂₁, NR₂₂R₂₃,CN, COR₂₁, COOR₂₁ or CONR₂₂R₂₃; R₁₁ and R₁₂ are independently from oneanother H, [C₂-C₆alkylene-O]_(n)C₁-C₁₂alkyl,[C₂-C₆alkylene-NH]_(n)C₁-C₁₂alkyl, C₁-C₁₂alkyl, C₃-C₁₂cycloalkyl,C₂-C₁₂alkenyl, C₃-C₁₂cycloalkenyl or C₂-C₁₂alkynyl, each of which isunsubstituted or substituted one or several times by Cl, F, OR₂₁,NR₂₂R₂₃, CN, COR₂₁, COOR₂₁ or CONR₂₂R₂₃; C₇-C₁₂aralkyl or C₆-C₁₂aryl,each of which is unsubstituted or substituted one or several times byNO₂, SOR₂₁, SO₂R₂₁, SO₃R₂₁, SO₂NR₂₂R₂₃, Br, Cl, F, OR₂₁, SR₂₁, NR₂₂R₂₃,CN, COR₂₁, COOR₂₁ or CONR₂₂R₂₃; or NR₁₁R₁₂ is a 5-, 6- or 7-membered,saturated, unsaturated or aromatic, heterocyclic N-radical comprising C,N, O and/or S atoms, which heterocyclic N-radical may optionally beannellated with a cyclohexane, cyclohexene or benzene ring and isunsubstituted or substituted one or several times by oxo, hydroxy,C₁-C₁₂alkoxy, thiono and/or R₁₀, two or more R₁₀ being identical ordifferent from each other, and which annellated benzene ring isunsubstituted or substituted by NO₂, SOR₂₁, SO₂R₂₁, SO₃R₂₁, SO₂NR₂₂R₂₃,Br, Cl, F, OR₂₁, NR₂₂R₂₃, CN, COR₂₁, COOR₂₁ or CONR₂₂R₂₃; R₁₃, R₁₄ andR₁₅ have independently from R₇, R₈ and R₉ the same definition as R₇, R₈and R₉, or R₁₃ is a direct bond from C in position 1 or 2 of theanthraquinone substructure to R₁₆; R₁₆, R₁₇, R₁₈, R₁₉ and R₂₀ haveindependently from R₁, R₂, R₃, R₄ and R₅ the same definition as R₁, R₂,R₃, R₄ and R₅, R₂₁, R₂₂ and R₂₃ are independently of one another H;[C₂-C₆alkylene-O]_(n)C₁-C₁₂alkyl, [C₂-C₆alkylene-NH]_(n)C₁-C₁₂alkyl orC₁-C₁₂alkyl which is unsubstituted or substituted one or several timesby F, oxo, OH, OC₁-C₆alkyl, NH₂, NHC₁-C₆alkyl, N(C₁-C₆alkyl)₂, COOH,COOC₁-C₆alkyl, CONHC₁-C₆alkyl, CON(C₁-C₆alkyl)₂ or CN; and n is aninteger 1, 2, 3, 4 or
 5. 2. A colourant composition according to claim1, wherein one or two of R₁, R₂ and R₃ are H, and R₄ and R₅ are both H;one of R₁, R₂ and R₃ is SOR₁₀, SO₂R₁₀, SO₃R₁₀, SO₂NR₁₁R₁₂, CN, COR₁₀,COOR₁₀ or CONR₁₁R₁₂; R₆, R₇, R₈, R₉, R₁₃, R₁₄ and R₁₅ are SO₃R₁₀,SO₂NR₁₁R₁₂, NO₂, C₁-C₁₂alkyl, Cl, F or H; and one or more of R₁₀, R₁₁ orR₁₂ a hydroxy group.
 3. A colourant composition according to claim 1,wherein the pigment is Colour Index Pigment Yellow 3, 7, 12, 13, 14, 17,24, 34, 42, 53, 62, 74, 83, 93, 95, 108, 109, 110, 111, 119, 123, 128,129, 138, 139, 147, 150, 164, 168, 173, 174, 180, 184, 188, 191, 191:1,191:2, 193, 199, Pigment Orange 5, 13, 16, 34, 40, 43, 48, 49, 51, 61,64, 71, 73, Pigment Red 2, 4, 5, 23, 48:1, 48:2, 48:3, 48:4, 52:2, 53:1,57, 57:1, 88, 89, 101, 104, 112, 122, 144, 146, 149, 166, 168, 177, 178,179, 181, 184, 190, 192, 194, 202, 204, 206, 207, 209, 214, 216, 220,221, 222, 224, 226, 254, 255, 262, 264, 270, 272, 282, 283, PigmentBrown 23, 24, 33, 42, 43, 44, Pigment Violet 19, 23, 29, 31, 37, 42,Pigment Blue 15, 15:1, 15:2, 15:3, 15:4, 15:6, 16, 25, 26, 28, 29, 60,64, 66, 80, Pigment Green 7, 17, 36, 37,50,3,6-di(3′-cyano-phenyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dione,3-phenyl-6-(4′-tert-butyl-phenyl)-2,5-dihydro-pyrrolo[3,4-c]pyrrole-1,4-dioneor Vat Red 74, or a mixture thereof.
 4. A colourant compositionaccording to claim 1, which is a photoresist composition.
 5. A compoundof formula (I) of claim 1, wherein at least one of R₁, R₂ and R₃ isSOR₁₀, SO₂R₁₀, SO₃R₁₀, SO₂NR₁₁R₁₂, CN, COR₁₀, COOR₁₀ or CONR₁₁R₁₂, or atleast one of R₆, R₇, R₈ and R₉ is SO₂NR₁₁R₁₂, with the proviso that thecompound is not of formula

or a compound of formula (II) of claim 1, wherein at least one of R₁, R₂and R₃ is SOR₁₀, SO₂R₁₀, SO₃R₁₀, SO₂NR₁₁R₁₂, CN, COR₁₀, COOR₁₀ orCONR₁₁R₁₂, or at least one of R₆, R₇, R₈ and R₉ is SO₂NR₁₁R₁₂, with theproviso that the compound is not of formula


6. A compound according to claim 5 of formula

wherein at least one of R₁, R₂ and R₃ is SOR₁₀, SO₂R₁₀, SO₃R₁₀,SO₂NR₁₁R₁₂, CN or COR₁₀, or at least one of R₇, R₈ and R₉ is SO₂NR₁₁R₁₂,with the proviso that R₃ is not SO₂NH₂.
 7. A photoresist compositioncomprising a compound according to claim
 5. 8. A colour filtercomprising a transparent substrate and one layer or multiple layersthereon, at least one layer being a patterned layer, the pattern ofwhich comprises a compound of formula (I) or (II) according to claim 1.9. A composition comprising from 0.1 to 70% by weight of a colourantcomposition according to claim 1 and a liquid medium comprising a binderor a polymerisable compound.
 10. A process for manufacturing a colourfilter, wherein a composition according to claim 9 is applied onto atransparent substrate optionally comprising patterned or not patternedlayers thereon, and the composition is dried and/or cured to give apatterned layer.
 11. A printing ink, plastic, coating, textile or paperproduct comprising a compound according to claim
 5. 12. (canceled)
 13. Acolourant composition according to claim 1 comprising in a weight ratioof from 95:5 to 30:70, a pigment of average particle size from 10 to 200nm and a compound of formula I or II.
 14. A colourant compositionaccording to claim 1 wherein R₁₃, R₁₄ and R₁₅ are each identical to R₇,R₈ and R₉, respectively and R₁₆, R₁₇, R₁₈, R₁₉ and R₂₀ are eachidentical to R₁, R₂, R₃, R₄ and R₅, respectively.
 15. A colour filtercomprising a transparent substrate and one layer or multiple layersthereon, at least one layer being a patterned layer, the pattern ofwhich comprises a compound of formula (III) or (IV) according to claim5.